Pyridine → 4-dipropylamino-N methylthio-N-methyl-3,5-dinitrobenzenesulfonamide
Reaction equation
[CH3:1][S:2]Cl.[CH2:4]([N:7]([CH2:25][CH2:26][CH3:27])[C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]([S:17]([NH:20][CH3:21])(=[O:19])=[O:18])=[CH:10][C:9]=1[N+:22]([O-:24])=[O:23])[CH2:5][CH3:6].N1C=CC=CC=1>ClCCl>[CH2:25]([N:7]([CH2:4][CH2:5][CH3:6])[C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]([S:17]([N:20]([S:2][CH3:1])[CH3:21])(=[O:19])=[O:18])=[CH:10][C:9]=1[N+:22]([O-:24])=[O:23])[CH2:26][CH3:27]Participants
Procedure
A 1.1 g (0.012 mol) sample of methylsulfenyl chloride was added dropwise to a cooled (-5° to -10° C.) solution of 3.6 g (0.01 mol) 4-dipropylamino-N-methyl-3,5-dinitrobenzenesulfonamide and 1.1 g (0.014 mol) pyridine in 25 ml dichloromethane. The reaction mixture was then stirred at about 0° C. until the sulfonamide reactant could not be detected by thin layer chromatography on silica gel (benzene/acetone eluant). The reaction mixture was then washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give a yellow semi-solid residue. The residue was recrystallized from ethanol to give 2.3 g of the product, as a yellow solid, m.p. 119°-121° C. Elemental analysis for C14H22N4O6S2 showed: % S, calc. 15.8, found 15.9.
Workup
- washThe reaction mixture was then washed with water
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
- customto give a yellow semi-solid residue
- customThe residue was recrystallized from ethanol
Sources & evidence
- ORD record
- ord-985486c3eb07477ca03e50eb93e5d472
- Source dataset
- uspto-grants-1977_08
- Patent number
- US04041159
Reaction notes
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