Dimethylamine → N-tert.-butyl-2-dimethylaminocarbonyl-5-nitro-benzenesulfonamide

HRID 581663

Reaction equation

[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:18](OC)=[O:19])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][NH:23][CH3:24]>CO>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:18]([N:23]([CH3:24])[CH3:22])=[O:19])(=[O:8])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 35 °C

Procedure

115 g of N-tert.-butyl-2-methoxycarbonyl-5-nitro-benzenesulfonamide (Example c) in 1500 ml of methanol are gassed with about 200 g of dimethylamine. The mixture is stirred at about 35° C. for one week. The solution is concentrated under reduced pressure, the residue is taken up in ethyl acetate and the mixture is washed successively with dilute hydrochloric acid, saturated NaHCO3 solution and saturated NaCl solution. After drying over MgSO4, the organic phase is concentrated. 92 g of N-tert.-butyl-2-dimethylaminocarbonyl-5-nitro-benzensulfonamide are obtained: m.p.: 138-141° C.

Workup

concentrationThe solution is concentrated under reduced pressure
washthe mixture is washed successively with dilute hydrochloric acid, saturated NaHCO3 solution and saturated NaCl solution
dry with materialAfter drying over MgSO4
concentrationthe organic phase is concentrated

Sources & evidence

ORD record: ord-acded5627ff04c47b809c9982851e0f7
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922646

Linked notes

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