2-Fluoroaniline → Ethyl 3-{[(2-fluorophenyl)amino]sulfonyl}benzoate

HRID 400494Notes

Reaction equation

HRID 400494 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]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19]>CN(C)C(=O)C.C(OCC)(=O)C>[F:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH:19][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]

Participants

5

Reactant 2

HCID 95842-FluoroanilineHCID 19790734Ethyl 3-(chlorosulfonyl)benzoate

Product 1

HCID 66676185Ethyl 3-{[(2-fluorophenyl)amino]sulfonyl}benzoate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To ethyl 3-(chlorosulfonyl)benzoate (1 g, 4.02 mmol) in N,N-dimethylacetamide (13.4 mL) was added 2-fluoroaniline (1.551 mL, 16.08 mmol) dropwise over 1 minute at room temperature. The mixture was stirred at room temperature for 1 hour and then diluted with ethyl acetate (35 mL). The organic solution was washed with 1 N HCl (2×13 mL) and saturated NaCl (13 mL). The organic layer was concentrated, ethanol (38 mL) was added to the reside, and the mixture was concentrated to give ethyl 3-{[(2-fluorophenyl)amino]sulfonyl}benzoate.

Workup

  1. washThe organic solution was washed with 1 N HCl (2×13 mL) and saturated NaCl (13 mL)
  2. concentrationThe organic layer was concentrated
  3. additionethanol (38 mL) was added to the reside
  4. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-2bc5d3ea59ff4324a98889d93d2ff70b
Source dataset
uspto-grants-2014_06
Patent number
US08741899B2

Reaction notes

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