HCID 70056403, compound → Methyl 4,5,6,7-tetrahydro-1-methyl-1H-benzimidazole-5-carboxylate
Reaction equation
S(O)(O)(=O)=O.[CH3:6][N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][C:10]=2[N:9]=[CH:8]1>[C].[Rh].C(O)(=O)C>[CH3:6][N:7]1[C:11]2[CH2:12][CH2:13][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:15][C:10]=2[N:9]=[CH:8]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
In an autoclave 6.6 g (22.9 mmols) of methyl 1-methylbenzimidazole-5-carboxylate sulfate, 60 ml of acetic acid and 3.0 g of 5% rhodium-carbon powders were charged and hydrogenation was carried out at 80° C. for 92 hours under 60 atms. After cooling, rhodium-carbon powders were filtered off and the filtrate was distilled off under reduced pressure. After 200 ml of water was added to the residue, 1 N sodium hydroxide solution was added to the mixture at 0° to 5° C. to adjust pH to 9 to 10 followed by extraction with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and the solvent was distilled off to give 3.45 g (77.7%) of methyl 1-methyl-4,5,6,7-tetrahydrobenzimid-azole-5-carboxylate (oil).
Workup
- temperatureAfter cooling
- filtrationrhodium-carbon powders were filtered off
- distillationthe filtrate was distilled off under reduced pressure
- additionAfter 200 ml of water was added to the residue, 1 N sodium hydroxide solution
- additionwas added to the mixture at 0° to 5° C.
- extractionfollowed by extraction with ethyl acetate
- dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-11dd7937fc9942a8824dffc8f38af480
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04977175
Reaction notes
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