Hydrogen Bromide → 2-(3,4-Dichlorophenyl)-6,7-dinitroquinoxaline

HRID 584676

Reaction equation

HRID 584676 reaction equation
Br.[CH3:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)=O.[N+:13]([C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([NH2:25])=[C:18]([NH2:26])[CH:17]=1)([O-:15])=[O:14]>CS(C)=O>[Cl:12][C:7]1[CH:6]=[C:5]([C:3]2[CH:2]=[N:26][C:18]3[C:19](=[CH:20][C:21]([N+:22]([O-:24])=[O:23])=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=3)[N:25]=2)[CH:10]=[CH:9][C:8]=1[Cl:11]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 75841Ethanone, 1-(3,4-dichlorophenyl)-HCID 44419034,5-Dinitrobenzene-1,2-diamine

Product 1

HCID 223412132-(3,4-Dichlorophenyl)-6,7-dinitroquinoxaline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

48% aqueous HBr (8.8 M) (3.4 ml, 30 mmol) was slowly added to a stirred solution of 3,4-dichloroacetophenone (1.89 g, 10 mmol) in DMSO (17 ml). The solution was stirred in an open flask at 55° C. for 24 hours. The solution was poured onto ice, the solid product was filtered, washed with water, and redissolved in ethanol (18 ml). 4,5-Dinitro-1,2-phenylene-diamine (890 mg, 4.5 mmol) was added and the mixture was heated to reflux for 4 hours.

Workup

  1. additionThe solution was poured onto ice
  2. filtrationthe solid product was filtered
  3. washwashed with water
  4. dissolutionredissolved in ethanol (18 ml)
  5. temperaturethe mixture was heated
  6. temperatureto reflux for 4 hours

Sources & evidence

ORD record
ord-a20703e9de084538bfee31fbd1896e79
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Linked notes

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