Ammonium Hydroxide → 2-[1-(3-Bromo-phenyl)-1H-imidazol-4-yl]-1H-benzoimidazole

HRID 2266410Notes

Reaction equation

HRID 2266410 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([C:13](O)=O)[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[NH4+:16].[OH-]>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([C:13]3[NH:8][C:4]4[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=4[N:16]=3)[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 234449541-(3-Bromophenyl)-1H-imidazole-4-carboxylic acid

Product 1

HCID 161285902-[1-(3-Bromo-phenyl)-1H-imidazol-4-yl]-1H-benzoimidazoleYield 38%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

1-(3-Bromo-phenyl)-1H-imidazole-4-carboxylic acid 5 (150 mg, 0.56 mmol) was added to PPA (preheated to 140° C.) and the mixture was stirred until a thick homogeneous solution was obtained. 1,2-Phenyldiamine (67 mg, 0.62 mmol) was added and the mixture was heated for 6 h at 200° C. After cooling to room temperature it was carefully diluted with 6% NH4OH aqueous solution until the pH=8. The precipitate formed was isolated by filtration, dissolved in little ethyl acetate and filtrated again. Concentration of the organic layer afforded 72 mg (38%) of the title compound as a purple solid. HRMS (ESI+): m/z=339.1949 [M+H]

Workup

  1. customwas obtained
  2. temperatureAfter cooling to room temperature it
  3. customThe precipitate formed
  4. customwas isolated by filtration
  5. filtrationfiltrated again

Sources & evidence

ORD record
ord-8b3642761373492a86470f7696ea0620
Source dataset
uspto-grants-2010_12
Patent number
US07858649B2

Reaction notes

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