2,6-Difluoroaniline → Ethyl 3-{[(2,6-difluorophenyl)amino]sulfonyl}benzoate

HRID 1951493Notes

Reaction equation

HRID 1951493 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]=[C:20]([F:24])[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]=[C:20]([F:24])[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 796472,6-DifluoroanilineHCID 19790734Ethyl 3-(chlorosulfonyl)benzoate

Product 1

HCID 66676178Ethyl 3-{[(2,6-difluorophenyl)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 (6 mL) was added 2,6-difluoroaniline (2.03 g, 15.8 mmol) dropwise at room temperature. The mixture was stirred at room temperature for 5 hours and then diluted with ethyl acetate (40 mL). The organic solution was washed with 1 N HCl(2×15 mL and 3×30 mL) and saturated NaCl (30 mL). The organics were concentrated, ethanol (10 mL) was added, and the mixture was concentrated to give ethyl 3-{[(2,6-difluorophenyl)amino]sulfonyl}benzoate.

Workup

  1. washThe organic solution was washed with 1 N HCl(2×15 mL and 3×30 mL) and saturated NaCl (30 mL)
  2. concentrationThe organics were concentrated
  3. additionethanol (10 mL) was added
  4. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-f72307dd06894102aabd642288ce078f
Source dataset
uspto-grants-2013_03
Patent number
US08404719B2

Reaction notes

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