N-(2-amino-4-(4-methyl-1H-imidazol-1-yl)phenyl)-3-iodo-4-methylbenzamide → 2-(3-Iodo-4-methylphenyl)-6-(4-methyl-1H-imidazol-1-yl)-1H-benzo[d]imidazole

HRID 706818Notes

Reaction equation

HRID 706818 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]2)[CH:5]=[CH:4][C:3]=1[NH:14][C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([I:23])[CH:17]=1>C(O)(=O)C>[I:23][C:18]1[CH:17]=[C:16]([C:15]2[NH:1][C:2]3[CH:7]=[C:6]([N:8]4[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]4)[CH:5]=[CH:4][C:3]=3[N:14]=2)[CH:21]=[CH:20][C:19]=1[CH3:22]

Participants

3

Reactant 1

HCID 86709560N-(2-amino-4-(4-methyl-1H-imidazol-1-yl)phenyl)-3-iodo-4-methylbenzamide

Product 1

HCID 867095612-(3-Iodo-4-methylphenyl)-6-(4-methyl-1H-imidazol-1-yl)-1H-benzo[d]imidazoleYield 65.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-(2-amino-4-(4-methyl-1H-imidazol-1-yl)phenyl)-3-iodo-4-methylbenzamide (0.16 g, 0.37 mmol) in 5 mL glacial acetic acid was refluxed for 8 hrs, and then the mixture was evaporated in vacuo, the residue was purified by chromatography on silica gel (CH2Cl2/CH3OH 97:3 to 94:6) to give 0.1 g product as pale yellow solid (65.3%). LC/MS: m/z [M+H]+ 415.0415.

Workup

  1. customthe mixture was evaporated in vacuo
  2. customthe residue was purified by chromatography on silica gel (CH2Cl2/CH3OH 97:3 to 94:6)

Sources & evidence

ORD record
ord-3e7b2aeac09c467b807600fa66d298d5
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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