Diethyl (ethoxymethylene)malonate → HCID 19843275, compound

HRID 2352539Notes

Reaction equation

HRID 2352539 reaction equation
[NH2:1][C:2]1[C:6]([O:7][CH2:8][CH3:9])=[CH:5][S:4][CH:3]=1.C(O[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[CH:13][NH:1][C:2]1[C:6]([O:7][CH2:8][CH3:9])=[CH:5][S:4][CH:3]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:19]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 12520022HCID 12520022, compound

Product 1

HCID 19843275HCID 19843275, compound

Procedure

A mixture of 3-amino-4-ethoxythiophene (10 g) and diethyl ethoxymethylenemalonate (15.1 g) was stirred at 95° in an apparatus set for distillation. When ethanol evolution ceased (3 hours) the mixture was cooled to ambient temperature and the semi-solid was triturated with boiling petroleum ether (b.p. 60°-80°, 50 ml) then the mixture diluted with more petroleum ether (b.p. 60°-80, 300 ml). The solid was collected, washed with petroleum ether (b.p. 60°-80°) and dried to give the novel compound diethyl[(4-ethoxy-3-thienyl)amino]methylenemalonate, m.p. 108°-109°.

Workup

  1. distillationset for distillation
  2. custom(3 hours)
  3. customthe semi-solid was triturated with boiling petroleum ether (b.p. 60°-80°, 50 ml)
  4. additionthe mixture diluted with more petroleum ether (b.p. 60°-80, 300 ml)
  5. customThe solid was collected
  6. washwashed with petroleum ether (b.p. 60°-80°)
  7. customdried

Sources & evidence

ORD record
ord-b327524dfa444464bd21e30bea152014
Source dataset
uspto-grants-1989_10
Patent number
US04877793

Reaction notes

Loading…