Ammonia → 7-Bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-1-methyl-1H-benzo[d]imidazol-6-amine

HRID 2299126Notes

Reaction equation

HRID 2299126 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([Br:12])=[C:8]([NH2:11])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.[NH3:13]>C(O)C(C)C>[CH3:1][N:2]1[C:6]2[C:7]([Br:12])=[C:8]([NH:11][C:1]3[NH:13][CH2:5][CH2:6][N:2]=3)[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 129684523-Methyl-4-bromo-5-aminobenzimidazole

Product 1

HCID 129684437-Bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-1-methyl-1H-benzo[d]imidazol-6-amineYield 93%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

A solution of 3-methyl-4-bromo-5-aminobenzimidazole (0.31 g, 1.4 mmol) and ISA (0.6 g, 4.5 mmol) in 10 ml of isobutanol was stirred at reflux for 12 h. Oily residue obtained was subjected to column chromatography (NH3 sat'd 20% isopropanol/EtOAc) to yield 0.39 g (1.3 mmol, 93%) of the desired product. The product obtained was converted to the fumarate salt and recrystallized from MeOH to afford 0.50 g (68%) of the product as a white solid: mp 209-210° C.; Anal. Calc. for C11H12N5Br.2.0C4H4O4. requires C, 43.36; H, 3.83; N, 13.31. Found: C, 43.66; H, 3.84; N, 13.10.

Workup

  1. temperatureat reflux for 12 h
  2. customOily residue obtained

Sources & evidence

ORD record
ord-205a7d44484142998104212fa7d928d1
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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