Hydrochloric Acid → N-(n-Butylamino)carbonyl-2-(N,N-dimethylaminosulfonyl)benzenesulfonamide

HRID 232528Notes

Reaction equation

[CH2:1]([N:5]=[C:6]=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:8][N:9]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([NH2:23])(=[O:22])=[O:21])(=[O:13])=[O:12])[CH3:10].C(N(S(C1C=CC=CC=1S(N)(=O)=O)(=O)=O)CC)C.C(=O)([O-])[O-].[K+].[K+].Cl>C(#N)C>[CH2:1]([NH:5][C:6]([NH:23][S:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[S:11]([N:9]([CH3:10])[CH3:8])(=[O:12])=[O:13])(=[O:21])=[O:22])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

18.6 g (0.18 mol) of n-butyl isocyanate were added dropwise at 25° C. to a suspension of 44.2 g (0.17 mol) of 2-[(N,N-dimethylamino)sulfonyl]benzenesulfonamide (prepared similarly to 2-[(N,N-diethylamino)sulfonyl]benzenesulfonamide in U.S. Pat. No. 4,310,346) in 450 ml of acetonitrile. After the addition of 25.4 g (0.18 mol) of potassium carbonate, the refluxed mixture was stirred for 3 hours. It was cooled to 0° C., after which 400 ml of ice/water were added, the pH was brought to 1 by adding concentrated hydrochloric acid and the precipitate formed was filtered off under suction, washed neutral with water and dried at 40° C. under reduced pressure from a water pump. 60.0 g of the title compound (99% of theory) were obtained in this manner as a pale yellow powder.

Workup

customthe precipitate formed
filtrationwas filtered off under suction
washwashed neutral with water
dry with materialdried at 40° C. under reduced pressure from a water pump

Sources & evidence

ORD record: ord-1d8797a417e848eaa2b03a9ddede0f2c
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05591694

Reaction notes

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