Trimethyl orthovalerate → 2-butyl-1H-thieno[3,4-d]imidazole
Reaction equation
[NH2:1][C:2]1[C:6]([NH2:7])=[CH:5][S:4][CH:3]=1.[C:8](OC)(OC)(OC)[CH2:9][CH2:10][CH2:11][CH3:12].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[CH2:9]([C:8]1[NH:1][C:2]2=[CH:3][S:4][CH:5]=[C:6]2[N:7]=1)[CH2:10][CH2:11][CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3,4-diaminothiophene (156 mg) in ethanol (10 ml) was added trimethyl orthovalerate (0.29 ml) and pyridinium p-toluenesulfonate (4 mg). The mixture was refluxed for one hour and concentrated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel developed by ethyl acetate to give 2-butyl-1H-thieno[3,4-d]imidazole (155 mg) as crystals.
Workup
- temperatureThe mixture was refluxed for one hour
- concentrationconcentrated in vacuo
- customThe residue was purified by preparative thin layer chromatography on silica gel
Sources & evidence
- ORD record
- ord-354f919044724ce2b749849551db4a26
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05210092
Reaction notes
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