Dimethylamine → 4-Bromo-N,N-dimethylbenzenesulphonamide

HRID 2239384Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][NH:13][CH3:14]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:13]([CH3:14])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 7396p-Bromobenzenesulfonyl chloride

Product 1

HCID 128184-Bromo-N,N-dimethylbenzenesulphonamide

Procedure

In an analogous manner to General Procedure A, 4-Bromobenzene sulfonyl chloride (0.40 g, 1.56 mmol) and dimethylamine (10 mL, 33% in ethanol) were stirred together for 16 hours. 4-bromo-N,N-dimethylbenzenesulfonamide (0.11 g) was provided after purification. MS (ESI) m/z 264. HPLC purity 100.0% at 210-370 mn, 8.3 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

Sources & evidence

ORD record: ord-8bb4d00d4d524038b2078003df1c822e
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723332B2

Reaction notes

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