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

HRID 1586802Notes

Reaction equation

HRID 1586802 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-cdb8c714869c4d2c9b568e2d829f100a
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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