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

HRID 429554Notes

Reaction equation

HRID 429554 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-9f85d324a17d450588fd206636db5183
Source dataset
uspto-grants-2001_11
Patent number
US06316637B1

Reaction notes

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