4-Chloro-1,2-diaminobenzene → HCID 178526863, compound

HRID 2064601Notes

Reaction equation

HRID 2064601 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[N+:10]([C:13]1[C:14]([C:18](O)=O)=[N:15][NH:16][CH:17]=1)([O-:12])=[O:11].[OH-].[NH4+]>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:18]([C:14]3[C:13]([N+:10]([O-:12])=[O:11])=[CH:17][NH:16][N:15]=3)=[N:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 72634-Chloro-1,2-diaminobenzeneHCID 14923Ammonium HydroxideHCID 178524956HCID 178524956, compound

Product 1

HCID 178526863HCID 178526863, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-chloro-benzene-1,2-diamine (500 mg) in hydrochloric acid (4N) was treated with 4-nitro-pyrazole-3-carboxylic acid (826 mg) then heated at reflux temperature, under nitrogen. The reaction mixture was cooled to room temperature when the pH was adjusted to 8 by addition of ammonium hydroxide and the mixture was extracted with ethyl acetate. The extracts were evaporated to give 5-chloro-2-(4-nitro-1H-pyrazol-3-yl)-1H-benzoimidazole.

Workup

  1. temperaturethen heated
  2. temperatureat reflux temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe extracts were evaporated

Sources & evidence

ORD record
ord-406ca91a63d34a558ae171a50b0390c4
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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