Oxalyl chloride → 4-pentyl-4H-thieno[3,2-b]pyrrole-5,6-dione
Reaction equation
[CH2:1]([NH:6][C:7]1[CH:11]=[CH:10][S:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:12](Cl)(=[O:16])[C:13](Cl)=[O:14]>CCOCC>[CH2:1]([N:6]1[C:13](=[O:14])[C:12](=[O:16])[C:8]2[S:9][CH:10]=[CH:11][C:7]1=2)[CH2:2][CH2:3][CH2:4][CH3:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-pentylthiophen-3-amine (7.30 g, 4.30 mmol) in ether (50.0 mL) was added a solution of oxalyl chloride (6.00 mL, 42.0 mmol) in ether (50.0 mL) slowly at −10° C. The reaction mixture was stirred at ambient temperature for 3 h and quenched with cold water. The organic layer was separated, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography to afford the title compound (5.10 g, 53%): MS (ES+) m/z 246.3 (M+23).