Water → N-(4-chloro-thiobenzoyl)-2-phenyl-acetamide

HRID 1410384Notes

Reaction equation

HRID 1410384 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:17]1([CH2:23][C:24](Cl)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:8][C:24](=[O:25])[CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[S:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 27348264-Chlorothiobenzamide

Product 1

HCID 22174859N-(4-chloro-thiobenzoyl)-2-phenyl-acetamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4-chlorothiobenzamide (0.519 g, 3.02 mmol) in acetone (5 mL) was added pyridine (0.367 mL, 4.53 mmol) and phenylacetyl chloride (0.480 mL, 3.63 mmol). The bright orange reaction mixture was heated to 55° C. for 1 hour. The reaction mixture was allowed to cool to room temperature, and water (20 mL) was added. The precipitate was removed by filtration, washed with water, and dried to provide 0.721 g (82%) of the product as a red solid: 1H NMR (CDCl3) δ 9.34 (br s, 1H), 7.50-7.22 (m, 9H), 3.96 (s, 2H) ppm.

Workup

  1. temperatureto cool to room temperature
  2. customThe precipitate was removed by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-be42f344062e4958a5d2767c83b06819
Source dataset
uspto-grants-2014_12
Patent number
US08921547B2

Reaction notes

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