Water → N'-(2-bromophenyl)sulfonyl-N,N-dimethylmethanimidamide

HRID 476302

Reaction equation

HRID 476302 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([NH2:19])(=[O:18])=[O:17].CN(C=O)C.S([O-])(O)(=O)=O.[Na+].O>>[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16](/[N:19]=[CH:3]/[N:4]([CH3:6])[CH3:5])(=[O:18])=[O:17]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 516919Sodium BisulfateHCID 28012632-Bromobenzenesulfonamide

Product 1

HCID 11779014N'-(2-bromophenyl)sulfonyl-N,N-dimethylmethanimidamideYield 96.6%

Procedure

1,1-Dimethoxy-N,N-dimethylmethanamine (14.6 mL, 104 mmol) was added to 2-bromobenzene-1-sulfonamide (20.4 g, 86.4 mmol) in DMF (56 mL, 720 mmol). The mixture was stirred at room temperature for about 90 minutes. A solution of sodium hydrogen sulfate (1.7 g, 14 mmol) in water (170 mL, 9400 mmol) was cooled to 0° C. and then added to the mixture. The precipitate was filtered, washed with water, and dried to yield 2-bromo-N-[1-dimethylaminometh-(E)-ylidene]benzenesulfonamide as a white solid (24.3 g).

Workup

  1. additionadded to the mixture
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a55131d25bf24983896e2de344fa6d8a
Source dataset
uspto-grants-2014_01
Patent number
US08637676B2

Linked notes

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