Diethyl (ethoxymethylene)malonate → HCID 4048131, compound

HRID 1248187Notes

Reaction equation

HRID 1248187 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.C(O[CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])C>C(O)C>[S:3]1[CH:4]=[N:5][N:6]=[C:2]1[NH:1][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 199091,3,4-Thiadiazol-2-amine

Product 1

HCID 4048131HCID 4048131, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-amino-1,3,4-thiadiazole (5 g) was reacted with diethyl ethoxymethylenemalonate (26.5 g) in ethanol (20 ml) at the reflux temperature for 23 hours. After cooling the precipitate was filtered and purified with hexane to give diethyl N-(1,3,4-thiadiazol-2-yl)-aminomethylenemalonate, m.p. 107°-111° C. (10 g), which was treated with polyphosphoric acid (57.6 g; 30.8 g of 99% H3PO4 and 26.8 g of P2O5) and POCl3 (25 g) under stirring at 120° C. for 30 minutes.

Workup

  1. temperatureAfter cooling the precipitate
  2. filtrationwas filtered
  3. custompurified with hexane

Sources & evidence

ORD record
ord-8b3950e0de2f4cb18356359029486ee3
Source dataset
uspto-grants-1985_06
Patent number
US04522944

Reaction notes

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