Dimethylamine → N,N-Dimethyl-1H-benzimidazol-2-amine

HRID 869553Notes

Reaction equation

HRID 869553 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[CH3:11][NH:12][CH3:13].O>CN(C=O)C>[CH3:11][N:12]([CH3:13])[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 785722-Chlorobenzimidazole

Product 1

HCID 17846N,N-Dimethyl-1H-benzimidazol-2-amineYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

[step 1] Commercially available 2-chloro-1H-benzo[d]imidazole (250 mg, 1.64 mmol) was dissolved in DMF (4.7 mL), dimethylamine (50% aqueous solution, 0.50 mL, 4.92 mmol) was added, and the mixture was stirred with heating at 200° C. for 30 min in an Emrys Optimizer microwave synthesizer. Water was added to the mixture, and the precipitated crystals were collected by suction filtration to give N,N-dimethyl-1H-benzo[d]imidazole-2-amine (234 mg, 89%).

Workup

  1. filtrationthe precipitated crystals were collected by suction filtration

Sources & evidence

ORD record
ord-4b5530a2e1c84b01a6ac34fd38369dba
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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