Ethyl 2-azido-3-(2-thienyl)propenoate → ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 1017729Notes

Reaction equation

HRID 1017729 reaction equation
[N:1]([C:4](=[CH:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>C1(C)C(C)=CC=CC=1>[S:12]1[C:11]2[CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:1][C:15]=2[CH:14]=[CH:13]1

Participants

3

Reactant 1

HCID 54362140Ethyl 2-azido-3-(2-thienyl)propenoate

Product 1

HCID 292163ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylateYield 66.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of ethyl 2-azido-3-(2-thienyl)propenoate (0.45 g) in xylene (10 ml) was heated at reflux for 30 minutes, concentrated in vacuo and the residue purified by column chromatography using isohexane-15% ethyl acetate as eluent to give the product as a pale yellow solid (0.26 g, 66%), NMR d(CDCl3) 1.40 (3H, t), 4.39 (2H, q), 6.98 (1H, d), 7.18 (1H, s), 7.35 (1H, d), 9.30 (1H, bs) M/z (−) 194 (M-H+), 166.

Workup

  1. temperatureat reflux for 30 minutes
  2. concentrationconcentrated in vacuo
  3. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-a39e25ed253746e2a300e0fa1313e708
Source dataset
uspto-grants-2002_11
Patent number
US06479527B1

Reaction notes

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