Diethyl (ethoxymethylene)malonate → HCID 14278965, compound

HRID 868159Notes

Reaction equation

HRID 868159 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][N:12]=[C:11]([NH2:23])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH:27]=[C:28]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30])C>>[C:1]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][N:12]=[C:11]([NH:23][CH:27]=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 14278963HCID 14278963, compound

Product 1

HCID 14278965HCID 14278965, compound

Conditions

Temperature
120 °C

Procedure

A suspension of 4,5-bis(phenylmethoxy)-2-pyridinamine (8.7 g, 28.4 mmol) in diethyl ethoxymethylenemalonate (61.4 g, 284.0 mmol) was heated to 120° C. (bath temperature) for 2 hours. The major part of the diethyl ethoxymethylenemalonate was distilled off in vacuo and 100 ml of ether was added after cooling. The mixture was stored in the refrigerator overnight. The resulting crystals were filtered off with suction, washed with ether and dried in vacuo. Yield: 10.81 g; melting point 117.3° C.

Workup

  1. distillationThe major part of the diethyl ethoxymethylenemalonate was distilled off in vacuo and 100 ml of ether
  2. additionwas added
  3. temperatureafter cooling
  4. customwas stored in the refrigerator overnight
  5. filtrationThe resulting crystals were filtered off with suction
  6. washwashed with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-5d935428cec345a68e5576a9279a4c6f
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

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