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

HRID 504253

Reaction equation

HRID 504253 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[CH3:12][N:13]([CH:15]=O)[CH3:14].COC(OC)N(C)C.S([O-])(O)(=O)=O.[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](/[N:11]=[CH:12]/[N:13]([CH3:15])[CH3:14])(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 516919Sodium BisulfateHCID 28012632-Bromobenzenesulfonamide2×

Product 1

HCID 11779014N'-(2-bromophenyl)sulfonyl-N,N-dimethylmethanimidamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material, 2-bromobenzene-1-sulfonamide, is commercially available. Reaction of 2-bromobenzene-1-sulfonamide in a solvent such as DMF, with 1,1-dimethoxy-N,N-dimethylmethanamine, followed by the addition of sodium hydrogen sulfate in water, yields 2-bromo-N-[1-dimethylaminometh-(E)-ylidene]benzenesulfonamide. This compound is reacted with 4-methylphenylboronic acid to yield 4′-methylbiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide, then the —(CH2)r-L1 moiety is added, for example, by a halogenation reaction, to form compound (1).

Sources & evidence

ORD record
ord-832338c84b624ff2a506f34c4913433a
Source dataset
uspto-grants-2010_08
Patent number
US07777077B2

Linked notes

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