Reaction #1583889

ord-7336ff0144fa4c4082f6b8b573a108a3

Reaction equation

NS(=O)(=O)c1ccccc1Br
2-bromobenzene-1-sulfonamide
NS(=O)(=O)c1ccccc1Br
2-bromobenzene-1-sulfonamide
CN(C)C=O
DMF
COC(OC)N(C)C
1,1-dimethoxy-N,N-dimethylmethanamine
O=S(=O)([O-])O.[Na+]
sodium hydrogen sulfate
→
CN(C)/C=N/S(=O)(=O)c1ccccc1Br
2-bromo-N-[1-dimethylaminometh-(E)-ylidene]benzenesulfonamide

Reactants

NS(=O)(=O)c1ccccc1Br
2-bromobenzene-1-sulfonamide
NS(=O)(=O)c1ccccc1Br
2-bromobenzene-1-sulfonamide
CN(C)C=O
DMF
COC(OC)N(C)C
1,1-dimethoxy-N,N-dimethylmethanamine
O=S(=O)([O-])O.[Na+]
sodium hydrogen sulfate

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

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 (1f).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09198899B2uspto-grants-2015_12