4-Bromoaniline → N-(4-Bromophenyl)-1-methyl-1H-benzo[d]imidazol-2-amine

HRID 432245Notes

Reaction equation

HRID 432245 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1>>[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[N:6]([CH3:7])[C:5]3[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=3[N:3]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 78074-BromoanilineHCID 6630802-chloro-1-methyl-1H-1,3-benzodiazole

Product 1

HCID 924394N-(4-Bromophenyl)-1-methyl-1H-benzo[d]imidazol-2-amineYield 96.5%

Conditions

Temperature
170 °C

Procedure

A mixture of 2-chloro-1-methyl-benzimidazole (0.639 g, 3.84 mmol) and 4-bromoaniline (0.710 g, 4.12 mmol) was heated at 170° C. for 21 h. The resulting brown solid was cooled to room temperature, washed with three 5-mL portions of heptane, and then triturated with toluene to afford N2-(4-bromophenyl)-1-methyl-1H-benzo[d]imidazol-2-amine (1.120 g, 90%) as a brown powder. RP-HPLC (25 to 100% CH3CN in 0.1 N aqueous ammonium acetate over 10 min at 1 mL/min using a Hypersil HS C18, 250×4.6 mm column) tr=10.85 min, 96%; m/z 302 (MH+).

Workup

  1. temperatureThe resulting brown solid was cooled to room temperature
  2. washwashed with three 5-mL portions of heptane
  3. customtriturated with toluene

Sources & evidence

ORD record
ord-4d50b3bed8a44cae9dab319f564321a0
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

Loading…