Diethyl (ethoxymethylene)malonate → HCID 13312968, compound

HRID 1248188Notes

Reaction equation

HRID 1248188 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:5][N:6]=1.C(O[CH:16]=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:4]2[S:3][C:2]([NH:1][CH:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:6][N:5]=2)[CH:8]=1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 1990375-(Pyridin-3-yl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 13312968HCID 13312968, compound

Conditions

Temperature
120 °C

Procedure

2-amino-5-(3-pyridyl)-1,3,4-thiadiazole (10 g) was reacted with diethyl ethoxymethylene-malonate (18 g) under stirring at 120° C. for 9 hours. After cooling the reaction mixture was crystallized from CH2Cl2 -isopropyl ether to give diethyl N-[5-(3-pyridyl)-1,3,4-thiadiazol-2-yl]-aminomethylene-malonate, m.p. 144°-145° C. (15.8 g) which was treated with polyphosphoric acid (6.6 g: 3.5 g of 99% H3PO4 and 3.1 g of P2O5) and POCl3 (27.8 g) under stirring at 120° C. for 40 minutes.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customwas crystallized from CH2Cl2 -isopropyl ether

Sources & evidence

ORD record
ord-df51239db42f4ea08767d946d3b787bd
Source dataset
uspto-grants-1985_06
Patent number
US04522944

Reaction notes

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