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

HRID 2104422Notes

Reaction equation

HRID 2104422 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:12]Cl)=[C:8]([CH2:10]Cl)[CH:9]=1)=[O:4].[CH3:14][NH2:15]>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[CH2:12][N:15]([CH3:14])[CH2:10][C:8]=2[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 11096691Methyl 4,5-bis(chloromethyl)thiophene-2-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,5-Bis(chloromethyl)-2-thiophenecarboxylic acid methyl ester (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 thereto, followed by stirring at room temperature for 3 days. The solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:methanol=1:0→19:1), to thereby give the title compound (176 mg).

Workup

  1. distillationThe solvent was distilled away under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=1:0→19:1)

Sources & evidence

ORD record
ord-b6bdf4364ec04d5b8ff19af3547de3ba
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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