2-Thiophenecarbonyl chloride → 4-Methyl-5-(thiophene-2-carbonyl)-1,3-dihydro-2H-imidazol-2-one

HRID 1995660Notes

Reaction equation

HRID 1995660 reaction equation
[CH3:1][C:2]1[CH:6]=[N:5][C:4](=[O:7])[N:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](Cl)=[O:18]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:1][C:2]1[NH:3][C:4](=[O:7])[NH:5][C:6]=1[C:17]([C:13]1[S:12][CH:16]=[CH:15][CH:14]=1)=[O:18]

Participants

5

Reactant 3

HCID 789282-Thiophenecarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 22290139HCID 22290139, compound

Product 1

HCID 155675464-Methyl-5-(thiophene-2-carbonyl)-1,3-dihydro-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7.3 g of 4-methylimidazol-2-one and 10.8 g of aluminum chloride in 150 ml of nitrobenzene is added 12.0 g of 2-thienoyl chloride. The mixture is stirred at 60° C. for 3 hours, cooled and poured over ice water. The organic portion is extracted into ethyl acetate, dried and the organic solvent evaporated to give the title compound. M.P. 212°-215° C.

Workup

  1. temperaturecooled
  2. extractionThe organic portion is extracted into ethyl acetate
  3. customdried
  4. customthe organic solvent evaporated

Sources & evidence

ORD record
ord-35150c29c8e54383be0cb3148ed6df80
Source dataset
uspto-grants-1983_09
Patent number
US04405635

Reaction notes

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