Methanesulfonyl chloride → HCID 10246753, compound
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[O:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[NH:1][S:21]([CH3:20])(=[O:23])=[O:22])[C:6]([NH2:8])=[O:7]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A mixture of 4-amino-3-(2,4-difluorophenoxy)benzamide (0.82 g) and methanesulfonyl chloride (0.39 g) in pyridine (5 ml) was stirred for 15 minutes at 5° C. and for 30 minutes at room temperature. Pyridine was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate, washed with diluted hydrochloric acid and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue (1.1 g) was subjected to column chromatography on silica gel (20 g) eluting with a mixture of toluene and ethyl acetate (1:2). The fractions containing the desired compound were combined and concentrated to give colorless crystals of 3-(2,4-difluorophenoxy)-4-(methanesulfonamido)benzamide (0.74 g).
Workup
- customPyridine was evaporated under reduced pressure
- dissolutionthe residue was dissolved in ethyl acetate
- washwashed with diluted hydrochloric acid
- dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- washeluting with a mixture of toluene and ethyl acetate (1:2)
- additionThe fractions containing the desired compound
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a050a57066e0487e810393db0f3e16f4
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04866091
Reaction notes
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