Methylamine → 1H-Benzimidazol-2-amine,N,1-dimethyl-(9CI)
Reaction equation
[I-].CO[N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N+:6]([CH3:13])=[CH:5]1.[CH3:14][NH2:15]>>[CH3:13][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]=[C:5]1[NH:15][CH3:14]Participants
3
Procedure
3-N-Alkoxyimidazolium salts are also known. For example, 3-N-methoxy-1-N-methylbenzimidazolium iodide has been shown to react with methylamine to afford 1-methyl-2-methylaminobezimidazole in approximately 20% yield (S. Takahashi et al., Chem. Pharm. Bull. 14(4):375-385 (1966)). While this reaction was reported to proceed under relatively mild conditions (i.e., 20°-25° C. for 1 hour), the difficulty in obtaining large quantities of 3-N-oxide starting material renders this approach to 2-substituted imidazoles particularly undesirable.
Sources & evidence
- ORD record
- ord-a3a1ffa487b74079aaa079dfac5d6285
- Source dataset
- uspto-grants-1998_10
- Patent number
- US05817823
Reaction notes
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