Benzoyl chloride → HCID 18185288, compound

HRID 1358742Notes

Reaction equation

HRID 1358742 reaction equation
[F:1][C:2]([F:13])([F:12])[S:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[F:13][C:2]([F:12])([F:1])[S:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH:9][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 27778754-(Trifluoromethylthio)benzylamine

Product 1

HCID 18185288HCID 18185288, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(trifluromethylthio)benzylamine (250 mg, 1.21 mmol), benzoyl chloride (178 mg, 1.27 mmol) and sodium bicarbonate (508 mg, 6.05 mmol) in DCM (15 mL) was stirred at rt until the reaction completed. The reaction was diluted with ethyl acetate, washed with brine and dried to give 372 mg (99%) of N-(4-trifluoromethylthiobenzyl)benzamide as a white solid. 1HNMR (360 MHz, DMSO-d6) δ 9.07 (m, 1H, NH), 7.88-7.90 (m, 2H), 7.66-7.68 (d, J=8.7 Hz, 2H), 7.45-7.56 (m, 5H), 4.53 (d, J=6.1 Hz, NCH2, 2H). MS-EI m/z 311 [M+].

Workup

  1. washwashed with brine
  2. customdried

Sources & evidence

ORD record
ord-389439435df2428ea1219c3a69776d70
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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