Methanesulfonyl chloride → 3-(2,4-Difluorophenylthio)-4-(methanesulfonamido)benzoic acid
Reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][C:3]=1[S:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[S:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[NH:1][S:23]([CH3:22])(=[O:25])=[O:24])[C:6]([OH:8])=[O:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of ethyl 4-amino-3-(2,4-difluorophenylthio)benzoate (1.1 g) and methanesulfonyl chloride (0.93 g) in pyridine (5 ml) was stirred at 60° C. for 2 hours. The reaction mixture was evaporated. The residue was dissolved in methanol and treated with potassium hydroxide (2 g). The mixture was concentrated and the residue was dissolved in water and washed with chloroform. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The solid residue was recrystallized from ethanol to give 3-(2,4-difluorophenylthio)-4-(methanesulfonamido)benzoic acid (0.66 g).
Workup
- customThe reaction mixture was evaporated
- dissolutionThe residue was dissolved in methanol
- additiontreated with potassium hydroxide (2 g)
- concentrationThe mixture was concentrated
- dissolutionthe residue was dissolved in water
- washwashed with chloroform
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- customdried
- customevaporated
- customThe solid residue was recrystallized from ethanol
Sources & evidence
- ORD record
- ord-fd53285f608047cd85045982a19482a6
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05034417
Reaction notes
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