Methanesulfonyl chloride → Phenyl 4-[(methylsulphonyl)amino]benzenemethanesulphonate
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][S:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])=[CH:10][CH:9]=1>N1C=CC=CC=1.CC(=O)OCC>[CH3:1][S:2]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][S:15]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:17])=[O:16])=[CH:10][CH:9]=1)(=[O:4])=[O:3]Participants
5
Procedure
Methanesulphonyl chloride (1.12 ml) was added to a cooled stirred solution of phenyl 4-aminobenzenemethanesulphonate, hydrochloride (3.0 g) in pyridine (9 ml). The resulting mixture was allowed to warm up to 20° and then stirred for 20 h. The reaction mixture was diluted with EA (150 ml) and washed with 8% NaHCO3 (400 ml), H2O (250 ml) and brine (250 ml). The organic extract was dried (MgSO4) and evaporated to leave a brown gum which was crystallised from toluene (100 ml) to give the crude title compound (as an off-white solid which was recrystallised from toluene (100 ml) to give the title compound (1.25 g) as a white solid m.p. 128°-129°.
Workup
- temperatureto warm up to 20°
- washwashed with 8% NaHCO3 (400 ml), H2O (250 ml) and brine (250 ml)
- extractionThe organic extract
- dry with materialwas dried (MgSO4)
- customevaporated
- customto leave a brown gum which
- customwas crystallised from toluene (100 ml)
- customto give the crude title compound (as an off-white solid which
- customwas recrystallised from toluene (100 ml)
Sources & evidence
- ORD record
- ord-ba971aa6446e44668ffa2c22bc9a4fc8
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04855314
Reaction notes
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