Category: 16313-66-9

Electric Literature of 16313-66-9,Some common heterocyclic compound, 16313-66-9, name is 2-Amino-5-bromobenzamide, molecular formula is C7H7BrN2O, 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: 3.3.1 6-Bromo-8-iodo-2-phenylquinazolin-4(3H)-one (4a) A stirred mixture of 2 (1.00 g, 2.94 mmol), benzaldehyde (0.37 g, 3.52 mmol) and iodine (1.49 g, 5.88 mmol) in ethanol (100 mL) was refluxed for 7 h and then allowed to cool to room temperature. The mixture was quenched with an ice-cold aqueous sodium thiosulfate solution and the precipitate was filtered and recrystallized to afford 4a as a white solid. 6-Bromo-2-(4-chlorophenyl)-8-iodoquinazolin-4(3H)-one (4c). A stirred mixture of 2 (1.00 g, 2.95 mmol), 4-chlorobenzaldehyde (0.49 g, 3.54 mmol) and iodine (1.49 g, 5.90 mmol) in ethanol (100 mL) afforded 4c as a white solid (1.24 g, 91%), mp. > 345 C; numax (ATR) 490, 526, 554, 686, 729, 791, 944, 1014, 1095, 1285, 1428, 1467, 1559, 1602, 1662, 3072, 3159 cm-1; deltaH (500 MHz, DMSO-d6) 7.66 (d, J = 9.0 Hz, 2H), 8.19 (d, J = 2.0 Hz, 1H), 8.28 (d, J = 9.0 Hz, 2H), 8.49 (d, J = 2.0 Hz, 1H), 12.91 (br s, 1H); deltaC (125 MHz, DMSO-d6) 103.4, 122.9, 128.3, 128.8, 128.9, 129.3, 130.2, 137.4, 144.3, 146.0, 147.9, 161.6; m/z 461 (100, MH+); HRMS (ES): MH+, found 460.8550. C14H879Br 35ClIN2O+ requires 460.8553.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-bromobenzamide, its application will become more common.

Reference:
Article; Paumo, Hugues K.; Mphahlele, Malose J.; Rhyman, Lydia; Ramasami, Ponnadurai; Tetrahedron; vol. 72; 1; (2016); p. 123 – 133;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16313-66-9, name is 2-Amino-5-bromobenzamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 16313-66-9, Recommanded Product: 16313-66-9

To a solution of compound 5-4-2 (22.0 g, crude product) in dry THF (250 mL), compound 1-19 (7.6 g, 35.5 mmol) and NaOH (1 M, 85.0 mmol) were added in turn. At the end of the addition, the mixture was stirred at rt for 1.0 hr. After the reaction was completed, the mixture was extracted with EtOAc (100 mL x 3). The combined organic layers were washed with NaOH aqueous solution (1 M.15 mL) and brine, dried over Na2S04and concentrated in vacuo to give the title compound (17.0 g, 100%). The compound was characterized by the following spectroscopic data:MS (ESI, pos.ion) mlz: 446.5 [M+H]’; and NMR (400 MHz. CDCL) delta (ppm): 9.06 (br, 1H), 7.75 (d, 1H).7.35.7.33 (d. d.1 H).7.28-7.22 (m, 5H). 6.69.6.67 (d. d.1H), 5.68 (brs.2H).5.14-5.13 (m, 2H).4.29-4.25 (m.1H), 3.66-3.60 (m, 1H), 3.45-3.37 (m. 1H), 2.39-2.32 (m.1H), 2.09-2.00 (m.1H), 1.96-1.77 (m, 2H).

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Reference:
Patent; SUNSHINE LAKE PHARMA CO.,LTD.; ZHANG, Jiancun; ZHANG, Yingjun; XIE, Hongming; REN, Qingyun; HU, Bailin; FU, Changping; WU, Xiwei; LI, Shifeng; WANG, Chenglin; ZHANG, Zhikeng; WO2014/82379; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 16313-66-9, name is 2-Amino-5-bromobenzamide, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H7BrN2O

12468] To a solution of compound 69-2 (22.0 g, crude product) in dry THF (250 mE), compound 69-5 (7.6 g, 35.5 mmol) and 1M NaOH (aq. 85 mE, 85 mmol) were added in turn. At the end of addition, the mixture was stirred at rt for 1 hr. After the reaction was completed, the mixture was extracted with EtOAc (100 mEx3). The combined organic layers were washed with 1M NaOH aqueous solution (15.0 mE) and brine, dried over Na2504 and concentrated in vacuo to give the title compound 6 9-6. The compound was characterized by the following spectroscopic data:12469] MS (ESI, pos.ion) mlz: 446.5 [M+H]12470] ?H NMR (400 MHz, CDC13) oe (ppm): 9.06 (br, 1H),7.75 (d, 1H), 7.35, 7.33 (d, d, 1H), 7.28-7.22 (m, 5H), 6.69,6.67 (d, d, 1H), 5.68 (brs, 2H), 5.14-5.13 (m, 2H), 4.29-4.25 (m, 1H), 3.66-3.60 (m, 1H), 3.45-3.37 (m, 1H), 2.39-2.32 (m, 1H), 2.09-2.00 (m, 1H), 1.96-1.77 (m, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16313-66-9.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD; Zhang, Yingjun; Zhang, Jaincun; Xie, Hongming; Ren, Qingyun; Tan, Yumei; Luo, Huichao; US2015/79028; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 16313-66-9,Some common heterocyclic compound, 16313-66-9, name is 2-Amino-5-bromobenzamide, molecular formula is C7H7BrN2O, 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 stirred solution of 2-amino-5-bromobenzamide (7.8 g, 0.036 mol), 4-methyl pentanoic acid (8.41 g, 0.O72mmol), and TBTU (17.46 g, 0.054 mol) in DMF (100 mL) was added DIPEA (25 mL, 0.154 mol) and the reaction mixture was stirred at room temperature for 14 h. The reaction mixture was diluted with water (100 mL)and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with aq. sodium bicarbonate solution (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate, and the volatiles were evaporated to dryness. The residue was purified by silica gel column chromatography using a gradient of 40% ethyl acetate in hexanes and the required fractions were collectedand volatiles were evaporated to give 5-bromo-2-(4-methylpentanamido)benzamide (7.0 g, 0.022 mol, 55% yield) as a brown solid. LCMS (ESI) m/e 313.0 (bromo pattern) [(M+H), calcd for C13H18BrN2O2, 313.05]; LC/MS retention time (LC/MS Method = Column – YMC PACK TMS (3X5Omm), 3.0 rim; Mphase A: 2%MeCN98%H20 – 10mM NH4OAc; Mphase B : 98%ACN – 2%H20 -10 mM NH4OAC;Flow: 1.2 mL/min)): ti = 2.12 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-bromobenzamide, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; MACOR, John E.; BRONSON, Joanne J.; DASGUPTA, Bireshwar; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; (226 pag.)WO2016/53794; (2016); 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. 16313-66-9, name is 2-Amino-5-bromobenzamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H7BrN2O

General procedure: 3.3.1 6-Bromo-8-iodo-2-phenylquinazolin-4(3H)-one (4a) A stirred mixture of 2 (1.00 g, 2.94 mmol), benzaldehyde (0.37 g, 3.52 mmol) and iodine (1.49 g, 5.88 mmol) in ethanol (100 mL) was refluxed for 7 h and then allowed to cool to room temperature. The mixture was quenched with an ice-cold aqueous sodium thiosulfate solution and the precipitate was filtered and recrystallized to afford 4a as a white solid (1.10 g, 87%), mp>345 C; numax (ATR) 527, 552, 636, 688, 698, 848, 946, 1129, 1291, 1384, 1446, 1470, 1563, 1598, 1658, 3073, 3164 cm-1; deltaH (500 MHz, DMSO-d6) 7.56-7.62 (m, 3H), 8.20 (d, J=2.0 Hz, 1H), 8.25-8.29 (m, 2H), 8.49 (d, J=2.0 Hz, 1H), 12.86 (s, 1H); deltaC (125 MHz, DMSO-d6) 103.5, 119.7, 122.9, 128.5, 128.9, 129.2, 132.4, 132.7, 145.9, 148.1, 153.7, 161.7; m/z 427 (100, MH+); HRMS (ES): MH+, found 426.8937. C14H979BrIN2O+ requires 426.8943.

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:
Article; Paumo, Hugues K.; Mphahlele, Malose J.; Rhyman, Lydia; Ramasami, Ponnadurai; Tetrahedron; vol. 72; 1; (2016); p. 123 – 133;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 16313-66-9, A common heterocyclic compound, 16313-66-9, name is 2-Amino-5-bromobenzamide, molecular formula is C7H7BrN2O, 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 dry 50 mL flask was charged with 2-aminobenzamides 1 (1.1 mmol), 5,5-dimethyl-1,3-cyclohexanedione 2 (0.280 g, 1.0 mmol), iodine (0.026 g, 0.01 mmol) and toluene (10.0 mL). The mixture was stirred at 80 C until the reactant 1 was consumed. After the completion of the reaction monitored by TLC, toluene was recovered by distillation under reduced pressure, and the residue was purified by silica column chromatography using ethyl acetate and petroleum ether (1:3) as the eluent to give products 5.

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:
Article; Lu, Lian; Zhang, Mei-Mei; Jiang, Hong; Wang, Xiang-Shan; Tetrahedron Letters; vol. 54; 8; (2013); p. 757 – 760;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics