Potassium Carbonate → 4H,5H,6H-thieno[2,3-c]pyrrol-6-one

HRID 1921819Notes

Reaction equation

HRID 1921819 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[CH2:10][NH2:11])=O.C([O-])([O-])=O.[K+].[K+]>CO.CCO>[S:6]1[C:5]2[C:3](=[O:2])[NH:11][CH2:10][C:9]=2[CH:8]=[CH:7]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 53419606Methyl 3-(aminomethyl)thiophene-2-carboxylate

Product 1

HCID 205428054H,5H,6H-thieno[2,3-c]pyrrol-6-one

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-aminomethyl-thiophene-2-carboxylic acid methyl ester (0.82 g, 4.79 mmol) in 1:1 MeOH-EtOH (125 mL), is added K2CO3 (0.66 g, 4.79 mmol) and the mixture is stirred at 90° C. for 5 hours. The solvent is removed in vacuo and the residue purified by silica gel column chromatography eluting with 97:3 DCM:MeOH. The title compound is isolated (0.365 g, 55%).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue purified by silica gel column chromatography
  3. washeluting with 97:3 DCM

Sources & evidence

ORD record
ord-79ebfa9aa570421ca3cd0e3c3a4a719c
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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