Trimethyl orthovalerate → 2-butyl-1H-thieno[3,4-d]imidazole

HRID 248380

Reaction equation

HRID 248380 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

HCID 83755Trimethyl orthovalerateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 643216Thiophene-3,4-diamine

Product 1

HCID 193706342-butyl-1H-thieno[3,4-d]imidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. temperatureThe mixture was refluxed for one hour
  2. concentrationconcentrated in vacuo
  3. 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

Linked notes

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