Water → HCID 66808394, compound

HRID 607249Notes

Reaction equation

HRID 607249 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.O.[CH2:11]([O:18][C:19]1[CH:36]=[CH:35][C:22]([O:23][C:24]2[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][C:25]=2[N+:32]([O-:34])=[O:33])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.OOS([O-])=O.[K+]>CN(C)C=O>[CH2:11]([O:18][C:19]1[CH:36]=[CH:35][C:22]([O:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]3[NH:9][C:4]4[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=4[N:8]=3)=[CH:26][C:25]=2[N+:32]([O-:34])=[O:33])=[CH:21][CH:20]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 3235934-Bromobenzene-1,2-diamineHCID 22120960HCID 22120960, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 66808394HCID 66808394, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-1,2-benzenediamine (214 mg, 1.145 mmol) in N,N-dimethylformamide (12 mL) containing water (0.4 mL) was treated with the product of Example 147A (400 mg, 1.145 mmol) and OXONE (458 mg, 0.7443 mmol), and the reaction stirred at room temperature for 30 minutes. Water (40 mL) was then added and the reaction stirred for 10 minutes. The mixture was vacuum filtered and the solid washed with water, then dried under vacuum. Purification by silica gel chromatography using a gradient of 3% to 4% ethyl acetate/methylene chloride as eluent provided the title compound as a yellow solid (305 mg, 51%).

Workup

  1. stirringthe reaction stirred for 10 minutes
  2. filtrationfiltered
  3. washthe solid washed with water
  4. customdried under vacuum
  5. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-c8ac34ff127c46eeabb538b2403d852f
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

Loading…