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

HRID 1951489Notes

Reaction equation

HRID 1951489 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:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20]>CN(C)C(=O)C.C(OCC)(=O)C>[F:16][C:17]1[CH:18]=[C:19]([NH:20][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:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 97423-FluoroanilineHCID 19790734Ethyl 3-(chlorosulfonyl)benzoate

Product 1

HCID 66676257Ethyl 3-{[(3-fluorophenyl)amino]sulfonyl}benzoate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To ethyl 3-(chlorosulfonyl)benzoate (1.0 g, 4.02 mmol) in N,N-dimethylacetamide (5 mL) was added 3-fluoroaniline (1.79 g, 16.08 mmol) dropwise over 30 seconds at room temperature. The mixture was stirred at room temperature for 4 hours, and then it was diluted with ethyl acetate (33 mL). The organic solution was washed with 1 N HCl (2×13 mL) and saturated NaCl (13 mL). The organic layer was concentrated, ethanol (8 mL) was added, and the mixture concentrated to give ethyl 3-{[(3-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 (8 mL) was added
  4. concentrationthe mixture concentrated

Sources & evidence

ORD record
ord-ef45ec4845324c2c8d7b54eed3529918
Source dataset
uspto-grants-2013_03
Patent number
US08404719B2

Reaction notes

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