ethyl 2-[[(4-methoxythiophen-3-yl)amino]methylidene]-3-oxohexanoate → 3-Methoxy-6-butyrylthieno[3,2-b]pyridin-7(4H)-one

HRID 2107627Notes

Reaction equation

HRID 2107627 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[C:18]([O:19][CH3:20])=[CH:17][S:16][CH:15]=1)[C:7]([O:9]CC)=O)(=[O:5])[CH2:2][CH2:3][CH3:4]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:20][O:19][C:18]1[C:14]2[NH:13][CH:12]=[C:6]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[C:7](=[O:9])[C:15]=2[S:16][CH:17]=1

Participants

3

Reactant 1

HCID 178450504ethyl 2-[[(4-methoxythiophen-3-yl)amino]methylidene]-3-oxohexanoate

Product 1

HCID 230461623-Methoxy-6-butyrylthieno[3,2-b]pyridin-7(4H)-one

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

To a refluxing solution of diphenyl ether (200 ml) was added ethyl 2-butyryl-3-(4-methoxy-3-thienylamino)-prop-2-enoate (16 g, 0.0539 mol) portionwise. On completion of the addition refluxing was continued for a further 20 minutes. The reaction mixture was allowed to cool and then diluted with petroleum ether to give a pale yellow solid, 11.85 g, m.p. 222°-225°.

Workup

  1. additionOn completion of the addition
  2. temperaturerefluxing
  3. temperatureto cool
  4. customto give a pale yellow solid, 11.85 g, m.p. 222°-225°

Sources & evidence

ORD record
ord-bf89ad7f071742f3a3da241316f1417e
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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