Category: 68524-30-1

68524-30-1,Some common heterocyclic compound, 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide, molecular formula is C15H15NOS, 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.

EXAMPLE 1; [0289 ] In this Example, the modafinil intermediate compound benzhydrylthioacetamide was oxidized to produce modafinil according to the processes described herein using various ratios of alcohol to organic acid and various reaction mixture temperatures.[0290] First, benzhydrylthioacetamide (10 g; MW = 257.35; 1.0 eq.), methanol, and acetic acid were charged to a 250 ml_ flask. Hydrogen peroxide (4.3 ml 1.05 eq.) was then charged to the resulting mixture over the course of about 5 minutes. The reaction was allowed to proceed for about 24 hours, with samples periodically taken for HLPC analysis. Several different trials using particular ratios of methanol and acetic acid at particular temperatures were performed. Results are illustrated in Tables 1-7, below.Table 1 : 20 ml_ methanol/20 mL acetic acid; 400CTable 2: 30 mL metha?ol/10 mL acetic acid; 400CTable 3: 35 mL methanol/5 mL acetic acid; 400C Table 4: 39 mL methanol/1 mL acetic acid; 400C [0291] As illustrated in Tables 1-7 above, the processes of the present invention are effective in producing modafinil at high yield and with relatively low sulfone impurity content. Specifically, as illustrated in Table 2, a reaction mixture comprising 30 mL of methanol and 10 mL acetic acid (i.e., methanol and acetic acid are present in the reaction mixture at a ratio of about 3:1 ) with the oxidation reaction proceeding at 400C is particularly effective, producing modafinil at about 96% yield with a sulfone impurity content of about 0.22%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-[(Diphenylmethyl)thio]acetamide, its application will become more common.

Reference:
Patent; MALLINCKRODT INC.; WO2007/70238; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 68524-30-1, These common heterocyclic compound, 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide, 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: VO(acac)2 (2 mol %) and ligand 6 or 10 (3 mol %) were dissolved in CHCl3 (145 muL). The solution turned slightly green-brown after stirring for 60 min. 2-(Benzhydrylthio)acetamide (30 mg, 0.12 mmol) was added, followed by the addition of aqueous H2O2 (30%, 1.2 equiv) in one portion. The reaction mixture was stirred at room temperature for a certain time (see Table 5, entries 2-7). The product was directly purified by column chromatography on silica gel (EtOAc). The isolated enantiomerically-enriched (R)-modafinil was identified through comparison of 1H NMR spectra with literature data (see Ref. 19). The enantiomeric excess of the product was determined by chiral HPLC analysis (Daicel Chiralpak AS, flow 0.9 mL/min, Hex/i-PrOH 60:40, 25 C, 31 bar).

The synthetic route of 68524-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stingl, Kerstin A.; Weiss, Katharina M.; Tsogoeva, Svetlana B.; Tetrahedron; vol. 68; 40; (2012); p. 8493 – 8501;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 68524-30-1,Some common heterocyclic compound, 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide, molecular formula is C15H15NOS, 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.

HTP Assay of CHMO Polypeptides: (0203) Primary screening used to guide optimization was carried out in a 200 muL volume in 96-well plate high-throughput (HTP) assay protocol using cell lysates. The general HTP assay conditions were: 1-100 g/L substrate (i.e., compound (1a) or (1b)), 10-200 muL of clear cell lysate containing the engineered CHMO polypeptide, 0.05-1.0 g/L NADP cofactor, 1 g/L ketoreductase (KRED) polypeptide for cofactor recycling, 0.025-0.100 M phosphate or TEA buffer solution containing 3.5%-10% (v/v) IPA (and optionally, 1.5% acetone or 10% PEG200) co-solvent, pH 8-9, 25 C. reaction temperature and 20 h reaction time (with 200 rpm shaking). The HTP assay conditions were changed slightly over the different rounds of the directed evolution of the CHMO variant polypeptide disclosed in order to detect those variants most improved in enzyme properties. Table 4 shows the HTP assay conditions used to perform primary screening of those variant polypeptides whose improved properties were confirmed by SFP assay as summarized in Tables 2A and 2B. Rounds 1-6 assays used the amide substrate of compound (1a) and Rounds 7-16 assays used the acid substrate of compound (1b). HTP Assay Results: (0220) Representative results in the primary screening using the HTP assay for both the amide substrate (compound (10) and the acid substrate (compound (2a)) are shown below in Tables 7 and 8.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-[(Diphenylmethyl)thio]acetamide, its application will become more common.

Reference:
Patent; CODEXIS, INC.; Ang, Ee Lui; Alvizo, Oscar; Behrouzian, Behnaz; Clay, Michael; Collier, Steven; Eberhard, Ellen; Fu, Fan Jaslyn; Song, Shiwei; Smith, Derek; Widegren, Magnus; Wilson, Robert; Xu, Junye; Zhu, Jun; (200 pag.)US9267159; (2016); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

68524-30-1, 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. 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Asymmetric synthesis of (-)-2-(diphenylmethyl)sulphinylacetamideGeneral procedure for examples 1 to 10 : Diphenylmethylthioacetamide (7.70 g ; 0.03 mol ; 1.0 eq) was dissolved in the solvent (toluene ; 77 mL ; 10 vol.) under argon. To the solution were added (S,S)-(-)-diethyl-tartrate (1.23 g ; 0.006 mol; 0.2 eq) and titanium (IV) tetraisopropoxide (0.85 g ; 0.88 mL ; 0.003 mol; 0.1 eq) and water (27 muL minus the sum of water present in reactants and solvent already introduced ; 0.0015 mol ; 0.05 eq) at 55C. In these conditions, the resulting chiral titanium complex has the stoichiometry (DET/Ti(OiPr)4/H2O : 2/1/0.5) and represents 0.1 eq of diphenylmethylthioacetamide. Stirring was maintained at 55C during 50 minutes. After cooling to room temperature (25C), were added to the mixture diisopropylethylamine (0.39 g ; 0.52 mL ; 0.003 mol ; 0.1 eq) and cumene hydroperoxide (4.55 g ; 5.0 mL ; 0.03 mol ; 1.0 eq). After contacting during about an hour, the formed precipitate is isolated by filtration. All the following experiments were performed in accordance with the conditions of the general procedure, by modifying parameters as indicated in tables 1-10.; Example 2 : Influence of the amount of water on the enantioselectivity of asymmetric oxidation In this experiment, the ratio of water was varied with respect to the titanium tetraisopropoxide from 0 to 1 equivalent, all the other parameters being as defined in the above general procedure. Notably, the ratio of the titanium chiral complex was maintained at 0.1 equivalent with respect to the diphenylmethylthioacetamide. [Table 2] EntryAmount of water (equivalent)E. e. (%)Purity (%)Yield (%)1080-90.320.493> 999230.894> 9988419199.590 – = Not determined These results show that the amount of water has an effect on the enantioselectivity of the reaction. Thus, the best enantioselectivities are achieved when an amount of water comprised between 0.4 and 0.8 equivalents are used. On the opposite, the enantioselectivity drops notably in the absence of water.

The synthetic route of 2-[(Diphenylmethyl)thio]acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEPHALON FRANCE; EP1516869; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

68524-30-1, 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. 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide, A new synthetic method of this compound is introduced below.

2-(Benzhydrylthio)acetamide obtained according to Example 4 (30 g-HPLC 97.9%) and acetic acid (120 ml) are loaded into a 1000 ml round-bottom flask. The mixture is heated to 40 C., slowly added with 35% hydrogen peroxide (11.7 g) and reacted at 40 C. for about 6 hours. The mixture is then cooled to 30 C., added with water (900 ml) and further cooled to 15 C. The product is filtered and washed with water. The wet product (49.4 g) thus obtained (HPLC: 95.73%, 0.083% (sulfone)) is dried at 50 C. under reduced pressure. Yield: 29.7 g. Crude modafinil is recrystallized from methanol (193 ml), by heating under reflux and cooling then to 15 C. The precipitate is filtered, washed with cold methanol and dried at 50 C. under reduced pressure. Yield: 23.4 g (HPLC: 99.9%, 0.01% (sulfone)).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; PROCOS S.P.A.; US2004/106829; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

68524-30-1,Some common heterocyclic compound, 68524-30-1, name is 2-[(Diphenylmethyl)thio]acetamide, molecular formula is C15H15NOS, 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.

EXAMPLE 1; [0289 ] In this Example, the modafinil intermediate compound benzhydrylthioacetamide was oxidized to produce modafinil according to the processes described herein using various ratios of alcohol to organic acid and various reaction mixture temperatures.[0290] First, benzhydrylthioacetamide (10 g; MW = 257.35; 1.0 eq.), methanol, and acetic acid were charged to a 250 ml_ flask. Hydrogen peroxide (4.3 ml 1.05 eq.) was then charged to the resulting mixture over the course of about 5 minutes. The reaction was allowed to proceed for about 24 hours, with samples periodically taken for HLPC analysis. Several different trials using particular ratios of methanol and acetic acid at particular temperatures were performed. Results are illustrated in Tables 1-7, below.Table 1 : 20 ml_ methanol/20 mL acetic acid; 400CTable 2: 30 mL metha?ol/10 mL acetic acid; 400CTable 3: 35 mL methanol/5 mL acetic acid; 400C Table 4: 39 mL methanol/1 mL acetic acid; 400C [0291] As illustrated in Tables 1-7 above, the processes of the present invention are effective in producing modafinil at high yield and with relatively low sulfone impurity content. Specifically, as illustrated in Table 2, a reaction mixture comprising 30 mL of methanol and 10 mL acetic acid (i.e., methanol and acetic acid are present in the reaction mixture at a ratio of about 3:1 ) with the oxidation reaction proceeding at 400C is particularly effective, producing modafinil at about 96% yield with a sulfone impurity content of about 0.22%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-[(Diphenylmethyl)thio]acetamide, its application will become more common.

Reference:
Patent; MALLINCKRODT INC.; WO2007/70238; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics