Methylamine → Methyl 5-methyl-5,6-dihydro-4H-thieno[2,3-c]pyrrole-2-carboxylate

Reaction equation

C[C:2]1[C:6]([CH2:7]Cl)=[C:5]([CH2:9]Cl)[S:4][C:3]=1[C:11]([OH:13])=[O:12].[CH3:14]N.[C:16](#[N:18])C>>[CH3:16][N:18]1[CH2:7][C:6]2[CH:2]=[C:3]([C:11]([O:13][CH3:14])=[O:12])[S:4][C:5]=2[CH2:9]1

Participants

Reactant 3

HCID 6329Methylamine

HCID 6342Acetonitrile

HCID 229370424,5-Bis(chloromethyl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 22937045Methyl 5-methyl-5,6-dihydro-4H-thieno[2,3-c]pyrrole-2-carboxylate

Procedure

Methyl 4,5-bis(chloromethyl)-2-thiophenecarboxylic acid (D. J. Zwanenburg and Hans Wynberg, J. Org. Chem., 34, 333-340, (1969)) (520 mg) was dissolved in acetonitrile (600 ml), methylamine (40% methanol solution, 722 μl) was added to the solution, and the mixture was stirred at room temperature for 3 days. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methylene chloride:methanol=1:0→19:1) to obtain the title compound (176 mg).