N-propylsulfamoyl chloride → methyl 2,6-difluoro-3-(N-propylsulfamoylamino)benzoate

HRID 1943961Notes

Reaction equation

HRID 1943961 reaction equation
[CH2:1]([NH:4][S:5](Cl)(=[O:7])=[O:6])[CH2:2][CH3:3].[NH2:9][C:10]1[C:11]([F:21])=[C:12]([C:17]([F:20])=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14]>C(Cl)Cl>[F:21][C:11]1[C:10]([NH:9][S:5](=[O:7])(=[O:6])[NH:4][CH2:1][CH2:2][CH3:3])=[CH:19][CH:18]=[C:17]([F:20])[C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 13398949N-propylsulfamoyl chlorideHCID 45480188Methyl 3-amino-2,6-difluorobenzoate

Product 1

HCID 67088999methyl 2,6-difluoro-3-(N-propylsulfamoylamino)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Propylsulfamoyl chloride (0.379 mL, 2.40 mmol) was added to methyl 3-amino-2,6-difluorobenzoate (0.150 mL, 0.802 mmol), TEA (0.335 mL, 2.40 mmol) in DCM (1.5 mL) at 0° C. The solution was warmed to room temperature overnight. The solids were filtered, and the supernate was concentrated to provide crude methyl 2,6-difluoro-3-(N-propylsulfamoylamino)benzoate, which was used directly in next step.

Workup

  1. filtrationThe solids were filtered
  2. concentrationthe supernate was concentrated

Sources & evidence

ORD record
ord-29e7be5fcf0a4f96bec987c88c9f1cec
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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