Methanol → N-tert-Butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide
Reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([NH:15][CH:16]=O)[CH:12]=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>C(Cl)(Cl)Cl>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([NH:15][CH3:16])[CH:12]=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
9.92 g (0.032 mol) of N-tert-butyl-5-formylamino-2-methoxycarbonylbenzenesulfonamide are dissolved in 50 ml of CHCl3, and then 5 ml (0.053 mol) of boranedimethyl sulfide complex are added at 0° C. After 1 h at 0° C. and 3 h at room temperature the reaction mixture is cooled to 0° C. 30 ml of methanol are added and the mixture is washed with water. The organic phase is dried over magnesium sulfate, the solvent is removed by distillation, and 9.23 g (98% of theory) of N-tert-butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide are obtained. m.p.: 120°-124° C.
Workup
- addition5 ml (0.053 mol) of boranedimethyl sulfide complex are added at 0° C
- washthe mixture is washed with water
- dry with materialThe organic phase is dried over magnesium sulfate
- customthe solvent is removed by distillation, and 9.23 g (98% of theory) of N-tert-butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide
- customare obtained
Sources & evidence
- ORD record
- ord-cfae78fceb714553a0b7edce08385c9b
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05449812
Reaction notes
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