Category: 98-18-0

Electric Literature of 98-18-0, A common heterocyclic compound, 98-18-0, name is 3-Aminobenzenesulfonamide, molecular formula is C6H8N2O2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

First the starting material, 3-isothiocyanato-benzenesulfonamide, which has the structural formula was prepared as follows. To a solution of 3-AMINO- benzenesulfonamide (Maybridge Chemical Co. , 1.00 g, 5.81 MMOL) in acetone (15 mL) at 0°C was added sequentially thiophosgene (0.503 mL, 6.39 MMOL) and fresh 25percent aq. NA2CO3 (5. 8 mL). The mixture was allowed to warm to ambient temperature. After 20 minutes, the acetone was removed under reduced pressure. The resultant suspension was adjusted to pH=7 with 10percent aq. HCI and filtered to isolate a light tan solid, 1.24 G (quantitative yield), that matched previous (mp 146-149°C ; French patent application FR 1528249; Chem. Abs. , 71, 30206 (1969) ) and was used without further purification. 1H NMR (DMSO-d6) : 87. 83-7.75 (1H, m), 7.69-7. 62 (1H, m), 7.52 (1H, s). The title compound was prepared in a manner similar to that for 4- [4-AMINO-5- (2- hydroxy-2-methyl-propionyl)-thiazol-2-ylamino]-benzenesulfonamide (Example M (1)). 3- ISOTHIOCYANATO-BENZENESULFONAMIDE (212 mg, 0.989 MMOL) furnished a yellow solid, 432 mg, that precipitated from IPROH/HEX to give 17. 1 mg of orange-brown solid. Furthermore, the mother liquor was purified via column, chromatography with a 5-10percent MeOH/CHCI3 stepwise gradient eluant to provide 120 mg of yellow solid that decomposed above 240 C. The total yield was 291 mg (73percent). 1H NMR (CD30D) : 8 8.36 (1H, dd, J = 1.8, 1.8 Hz), 7.78 (1H, ddd, J = 1.0, 2.2, 8.1 Hz), 7.62 (1H, ddd, J = 1. 1,1. 6,7. 8 HZ), 7.50 (1H, t, J = 8. 1 Hz), 7.05 (2H, t, J = 7. 5 HZ). FTIR (KBr): 3309,3076, 1620, 1546,1527, 1465,1429, 1156 cm-1. HRFABMS: Calcd for CR6H 3F2N403S2 (M+H+) 411.0406. Found: 411.0406. Anal. calcd. for CA6HR2F2N403S2 0. 5 H2O : C, 45.82 ; H, 3.12 ; N, 13.36 ; S, 15.29. Found: C, 45.78 ; H, 3.12 ; N, 13.18 ; S, 15.50.

The synthetic route of 98-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2004/72070; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 98-18-0, name is 3-Aminobenzenesulfonamide, A new synthetic method of this compound is introduced below., name: 3-Aminobenzenesulfonamide

A solution of 1-(2-methylsulfonyl-pyrimidin-4-yl)-1H-indazole (100 mg, 0.36 mmol) and p-toluenesulfonic acid (139 mg, 0.73 mmol) in i-PrOH (4 ml) was treated with 3-aminobenzene-sulfonamide (251 mg, 1.46 mmol) in a microwave synthesizer at 150° C. for 20 min. The mixture was partitioned between water and ethyl acetate, the organic layer separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was absorbed on silica gel and purified by flash chromatography (EtOAc/hexane, gradient from 30:70 to 50:50) to afford the title compound. This residue was triturated with aqueous NaOH (1 M), the solid collected by filtration, washed with water and dried under vacuum to afford 3-(4-indazol-1-ylpyrimidin-2-ylamino)-benzenesulfonamide (50 mg, 37percent yield). MS=367 [M+H]+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Roche Palo Alto LLC; US2008/146565; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 98-18-0, name is 3-Aminobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 98-18-0

A solution of 3-aminobenzenesulfonamide (271.9 mg, 1.58 mmol), 4,5- dichloro-2-fluoro-benzoic acid (300 mg, 1.43 mmol), and HATU (654.8 mg, 1.72 mmol) in DMF (3.12 mL) was treated with N-methylmorpholine (315.5 mu, 2.87 mmol) and stirred at 40 °C for 16 hours. The reaction was diluted with ethyl acetate and water and the organic layer separated. The organic layer was washed with 1 N HCl, water (3 x 50 mL), and brine, then dried over Na2S04, filtered, and concentrated. The residue was slurried in dichloromethane to form a white precipitate. The precipitate was filtered and washed with dichloromethane to provide 4,5-dichloro-2-fluoro-N-(3-sulfamoylphenyl)benzamide (422 mg, 81percent) as a white powder. 1H NMR (400 MHz, DMSO-d6) delta 10.85 (s, 1H), 8.32 – 8.25 (m, 1H), 8.03 (d, J = 6.7 Hz, 1H), 7.93 (d, J = 9.5 Hz, 1H), 7.83 (dt, J = 6.8, 2.2 Hz, 1H), 7.64 – 7.52 (m, 2H), 7.42 (s, 2H) ppm. ESI-MS m/z calc. 361.96948, found 364.7 (M+l)+; Retention time: 1.4 minutes (3 minutes run).

The synthetic route of 98-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HADIDA-RUAH, Sara Sabina; ANDERSON, Corey; TERMIN, Andreas P.; BEAR, Brian Richard; ARUMUGAM, Vijayalaksmi; KRENITSKY, Paul; JOHNSON, James Philip; WO2015/10065; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 98-18-0, A common heterocyclic compound, 98-18-0, name is 3-Aminobenzenesulfonamide, molecular formula is C6H8N2O2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A solution of intermediate (1.0 equiv.) in isopropanol, 1M hydrochloric acid (1.2 equiv.) and aniline (1.2 equiv.) were added. The reaction stirred at 90oC overnight in a sealed tube. Filtration and washed the resultant by cooled isopropanol, dried under vacuum. The solid was collected

The synthetic route of 98-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pobsuk, Nattakarn; Paracha, Tamkeen Urooj; Chaichamnong, Nattiya; Salaloy, Nattapas; Suphakun, Praphasri; Hannongbua, Supa; Choowongkomon, Kiattawee; Pekthong, Dumrongsak; Chootip, Krongkarn; Ingkaninan, Kornkanok; Gleeson, M. Paul; Bioorganic and Medicinal Chemistry Letters; vol. 29; 2; (2019); p. 267 – 270;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 98-18-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 98-18-0, name is 3-Aminobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 3-aminobenzenesulfonamide (413.3 mg, 2.40 mmol), 2,5- difluoro-4-methyl-benzoic acid (344.3 mg, 2.0 mmol), HATU (684.4 mg, 1.80 mmol) and N- methylmorpholine (439.8 mu, 4.0 mmol) in DMF (2 mL) was stirred at 40 °C for 2 hours. The reaction was poured into IN HCl and extracted with ethyl acetate (3x). The organics were combined, washed with water, brine, dried with Na2S04 and evaporated to dryness to give 2,5-difluoro-4-methyl-N-(3-sulfamoylphenyl)benzamide (610 mg, 94percent) as a solid that was used in the next step without further purification. ESI-MS m/z calc. 326.05, found 327.3 (M+1) +; Retention time: 1.25 minutes (3 minutes run).

The synthetic route of 3-Aminobenzenesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HADIDA-RUAH, Sara Sabina; ANDERSON, Corey; TERMIN, Andreas P.; BEAR, Brian Richard; ARUMUGAM, Vijayalaksmi; KRENITSKY, Paul; JOHNSON, James Philip; WO2015/10065; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 98-18-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 98-18-0, name is 3-Aminobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 3-aminobenzenesulfonamide (413.3 mg, 2.40 mmol), 2,5- difluoro-4-methyl-benzoic acid (344.3 mg, 2.0 mmol), HATU (684.4 mg, 1.80 mmol) and N- methylmorpholine (439.8 mu, 4.0 mmol) in DMF (2 mL) was stirred at 40 °C for 2 hours. The reaction was poured into IN HCl and extracted with ethyl acetate (3x). The organics were combined, washed with water, brine, dried with Na2S04 and evaporated to dryness to give 2,5-difluoro-4-methyl-N-(3-sulfamoylphenyl)benzamide (610 mg, 94percent) as a solid that was used in the next step without further purification. ESI-MS m/z calc. 326.05, found 327.3 (M+1) +; Retention time: 1.25 minutes (3 minutes run).

The synthetic route of 3-Aminobenzenesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HADIDA-RUAH, Sara Sabina; ANDERSON, Corey; TERMIN, Andreas P.; BEAR, Brian Richard; ARUMUGAM, Vijayalaksmi; KRENITSKY, Paul; JOHNSON, James Philip; WO2015/10065; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 98-18-0 as follows. category: amides-buliding-blocks

Scheme A[00230] A flask was charged with 3-aminobenzene sulfonamide (3.3 g, 19 mmol), and 20 mL of 1:1 acetone .1H2O. The solution was stirred at room temperature until the aminobenzene sulfonamide had dissolved. The flask was then cooled in an ice bath and dimethylamino-acetyl chloride HCl (4.6 g, 29 mmol) was added. To the resulting slurry sodium bicarbonate (4.8 g, 57 mmol) was added over a 15 m period. After 30 min the reaction was removed from the ice bath and allowed to stir at room temperature for 15 h. The reaction mixture was then filtered and washed with methanol and acetonitrile. The filtrate was dried on a rotary evaporator to yield 2-(dimethylamino)-JV-(3-sulfamoyl- phenyl)acetamide, which was submitted to the next step without further purification. MS (EI) m/z C10H15N3O3S: 258.0

According to the analysis of related databases, 98-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; WO2007/44729; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 98-18-0,Some common heterocyclic compound, 98-18-0, name is 3-Aminobenzenesulfonamide, molecular formula is C6H8N2O2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 3-aminobenzenesulfonamide (1.0 g, 5.81 mmol) and pyridine (4.7 mL, 58.07 mmol) in dichloromethane (10.3 mL) at 0 C was added dropwise 2,5-difluorobenzoyl chloride (719.3 mu, 5.81 mmol). The mixture was allowed to warm to 25 C and was stirred for 72 hours. The reaction mixture was diluted with ethyl acetate and water. The layers were separated and the organic layer washed with brine (2x). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give a clear oil that crystallized upon standing. The solid was re-dissolved in ethyl acetate and washed with IN HCl (3x). The organic layer was dried with MgS04, filtered and evaporated to yield 2,5-difluoro-N-(3-sulfamoylphenyl)benzamide (1.17 g, 64%) as a white solid. ESI- MS m/z calc. 312.04, found 313.3 (M+l) +; Retention time: 1.31 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) delta 10.81 (s, 1H), 8.31 (s, 1H), 7.84 (d, J = 9.1 Hz, 1H), 7.59 – 7.54 (m, 3H), 7.50 – 7.39 (m, 4H) ppm.

The synthetic route of 98-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HADIDA-RUAH, Sara Sabina; ANDERSON, Corey; TERMIN, Andreas P.; BEAR, Brian Richard; ARUMUGAM, Vijayalaksmi; KRENITSKY, Paul; JOHNSON, James Philip; WO2015/10065; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 98-18-0, A common heterocyclic compound, 98-18-0, name is 3-Aminobenzenesulfonamide, molecular formula is C6H8N2O2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

First the starting material, 3-isothiocyanato-benzenesulfonamide, which has the structural formula was prepared as follows. To a solution of 3-AMINO- benzenesulfonamide (Maybridge Chemical Co. , 1.00 g, 5.81 MMOL) in acetone (15 mL) at 0°C was added sequentially thiophosgene (0.503 mL, 6.39 MMOL) and fresh 25percent aq. NA2CO3 (5. 8 mL). The mixture was allowed to warm to ambient temperature. After 20 minutes, the acetone was removed under reduced pressure. The resultant suspension was adjusted to pH=7 with 10percent aq. HCI and filtered to isolate a light tan solid, 1.24 G (quantitative yield), that matched previous (mp 146-149°C ; French patent application FR 1528249; Chem. Abs. , 71, 30206 (1969) ) and was used without further purification. 1H NMR (DMSO-d6) : 87. 83-7.75 (1H, m), 7.69-7. 62 (1H, m), 7.52 (1H, s). The title compound was prepared in a manner similar to that for 4- [4-AMINO-5- (2- hydroxy-2-methyl-propionyl)-thiazol-2-ylamino]-benzenesulfonamide (Example M (1)). 3- ISOTHIOCYANATO-BENZENESULFONAMIDE (212 mg, 0.989 MMOL) furnished a yellow solid, 432 mg, that precipitated from IPROH/HEX to give 17. 1 mg of orange-brown solid. Furthermore, the mother liquor was purified via column, chromatography with a 5-10percent MeOH/CHCI3 stepwise gradient eluant to provide 120 mg of yellow solid that decomposed above 240 C. The total yield was 291 mg (73percent). 1H NMR (CD30D) : 8 8.36 (1H, dd, J = 1.8, 1.8 Hz), 7.78 (1H, ddd, J = 1.0, 2.2, 8.1 Hz), 7.62 (1H, ddd, J = 1. 1,1. 6,7. 8 HZ), 7.50 (1H, t, J = 8. 1 Hz), 7.05 (2H, t, J = 7. 5 HZ). FTIR (KBr): 3309,3076, 1620, 1546,1527, 1465,1429, 1156 cm-1. HRFABMS: Calcd for CR6H 3F2N403S2 (M+H+) 411.0406. Found: 411.0406. Anal. calcd. for CA6HR2F2N403S2 0. 5 H2O : C, 45.82 ; H, 3.12 ; N, 13.36 ; S, 15.29. Found: C, 45.78 ; H, 3.12 ; N, 13.18 ; S, 15.50.

The synthetic route of 98-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2004/72070; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 98-18-0, name is 3-Aminobenzenesulfonamide, A new synthetic method of this compound is introduced below., Computed Properties of C6H8N2O2S

A solution of 1-(2-methylsulfonyl-pyrimidin-4-yl)-1H-indazole (100 mg, 0.36 mmol) and p-toluenesulfonic acid (139 mg, 0.73 mmol) in i-PrOH (4 ml) was treated with 3-aminobenzene-sulfonamide (251 mg, 1.46 mmol) in a microwave synthesizer at 150° C. for 20 min. The mixture was partitioned between water and ethyl acetate, the organic layer separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was absorbed on silica gel and purified by flash chromatography (EtOAc/hexane, gradient from 30:70 to 50:50) to afford the title compound. This residue was triturated with aqueous NaOH (1 M), the solid collected by filtration, washed with water and dried under vacuum to afford 3-(4-indazol-1-ylpyrimidin-2-ylamino)-benzenesulfonamide (50 mg, 37percent yield). MS=367 [M+H]+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Roche Palo Alto LLC; US2008/146565; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics