Benzenamine, 2-(phenylsulfonyl)- → n-(2-Benzenesulfonyl-phenyl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramide

HRID 1358614Notes

Reaction equation

HRID 1358614 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.[F:26][C:27]([F:45])([F:44])[C:28]1[CH:29]=[C:30]([C:38]([CH3:43])([CH3:42])[C:39](Cl)=[O:40])[CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1>ClCCl>[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:39](=[O:40])[C:38]([C:30]2[CH:29]=[C:28]([C:27]([F:26])([F:44])[F:45])[CH:33]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:31]=2)([CH3:43])[CH3:42])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 77956Benzenamine, 2-(phenylsulfonyl)-HCID 81531DiisopropylethylamineHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chloride

Product 1

HCID 18185380n-(2-Benzenesulfonyl-phenyl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramideYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 233 mg (1.0 mmol) 2-aminophenyl phenyl sulfone and 0.25 ml (1.5 mmol) N-ethyldiisopropylamine in 2 ml dichloromethane was cooled in an ice bath and a solution of 350 mg (1.1 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 1 ml dichloromethane was added dropwise. The reaction mixture was stirred at room temperature overnight, evaporated and the residue was purified by flash chromatography to give 490 mg (95%) of the title compound as a pale yellow oil.

Workup

  1. customevaporated
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ec1dce1b6a524600a8004bc0f5832da3
Source dataset
uspto-grants-2003_07
Patent number
US06596773B2

Reaction notes

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