Reaction #1185

ord-bc7a243f2c2a4644a13ff947f64b4644

Reaction equation

BrBr
bromine
Cc1ccc(S(=O)(=O)Nc2ccc([N+](=O)[O-])cc2)cc1
N-(4-nitrophenyl)-4-methylbenzenesulphonamide
CC(C)[CH2][Mg][Cl]
isobutylmagnesium chloride
CCN(CC)CC
triethylamine
→
Br.Cc1ccc(S(=O)(=O)Nc2ccc(NN)c(CC(C)C)c2)cc1
expected product
Br.Cc1ccc(S(=O)(=O)Nc2ccc(NN)c(CC(C)C)c2)cc1
N-(4-Hydrazino-3-isobutylphenyl)-4-methylbenzenesulphonamide hydrobromide

Reactants

BrBr
bromine
—
solution
Cc1ccc(S(=O)(=O)Nc2ccc([N+](=O)[O-])cc2)cc1
N-(4-nitrophenyl)-4-methylbenzenesulphonamide
CC(C)[CH2][Mg][Cl]
isobutylmagnesium chloride
CCN(CC)CC
triethylamine

Reagents

None

Solvents

C1CCOC1
THF
CCOCC
ether

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThis compound is prepared

Procedure

This compound is prepared according to the procedure described in step A of Preparation 2.18, from 10 g of N-(4-nitrophenyl)-4-methylbenzenesulphonamide in 100 ml of THF and 42.6 ml of a 2M solution of isobutylmagnesium chloride in ether, followed by 4.4 ml of bromine and 23.4 ml of triethylamine. 5.9 g of the expected product are obtained, m.p.=170° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723483uspto-grants-1998_03