Diethyl (ethoxymethylene)malonate → Ethyl 2-ethoxycarbonyl-3-(4-methoxy-3-thienylamino)prop-2-enoate

HRID 2107621Notes

Reaction equation

HRID 2107621 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:8])=[CH:5][S:6][CH:7]=1.C(O[CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>C1(C)C=CC=CC=1>[CH2:22]([O:21][C:19]([C:13](=[CH:12][NH:8][C:4]1[C:3]([O:2][CH3:1])=[CH:7][S:6][CH:5]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 149896854-Methoxythiophen-3-amine

Product 1

HCID 23046153Ethyl 2-ethoxycarbonyl-3-(4-methoxy-3-thienylamino)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Methoxy-3-thiopheneamine (11.8 g, 0.091 mol) and diethyl ethoxymethylenemalonate (19.75 g, 0.091 mol) in toluene (300 ml) was heated under reflux in an atmosphere of nitrogen for 18 hours. The solvent was evaporated under reduced pressure to give a buff-coloured solid, this was washed with petroleum ether (b.p. 40°-60°) and the title compound collected by filtration, 25.23 g, m.p. 100°-102°.

Workup

  1. temperatureunder reflux in an atmosphere of nitrogen for 18 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customto give a buff-coloured solid
  4. washthis was washed with petroleum ether (b.p. 40°-60°)
  5. filtrationthe title compound collected by filtration, 25.23 g, m.p. 100°-102°

Sources & evidence

ORD record
ord-dc680d4812f240ba840e25f320b19e46
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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