4-(Trifluoromethyl)aniline → Ethyl 3-({[4-(trifluoromethyl)phenyl]amino}sulfonyl)benzoate

HRID 400510Notes

Reaction equation

HRID 400510 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:4])=[O:3].[F:16][C:17]([F:26])([F:25])[C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>CN(C)C(=O)C.C(OCC)(=O)C>[F:16][C:17]([F:25])([F:26])[C:18]1[CH:19]=[CH:20][C:21]([NH:22][S:2]([C:5]2[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:4])=[O:3])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 19790734Ethyl 3-(chlorosulfonyl)benzoate

Product 1

HCID 66675205Ethyl 3-({[4-(trifluoromethyl)phenyl]amino}sulfonyl)benzoate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To ethyl 3-(chlorosulfonyl)benzoate (4.0 g, 16.08 mmol) in N,N-dimethylacetamide (20 mL) was added 4-(trifluoromethyl)aniline (10.37 g, 64.3 mmol) dropwise at room temperature. The mixture was stirred at room temperature for 2.5 hours, and then it was diluted with ethyl acetate (130 mL). The organic solution was washed with 1 N HCl (2×60 mL) and saturated NaCl (60 mL). The organic layer was concentrated, ethanol (40 mL) was added, and the mixture was concentrated to give ethyl 3-({[4-(trifluoromethyl)phenyl]amino}sulfonyl)benzoate.

Workup

  1. washThe organic solution was washed with 1 N HCl (2×60 mL) and saturated NaCl (60 mL)
  2. concentrationThe organic layer was concentrated
  3. additionethanol (40 mL) was added
  4. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-da3c75eb16554233b273b4d185c5c602
Source dataset
uspto-grants-2014_06
Patent number
US08741899B2

Reaction notes

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