Diethyl (ethoxymethylene)malonate → HCID 13312969, compound

HRID 1248190Notes

Reaction equation

HRID 1248190 reaction equation
[NH2:1][C:2]1[S:3][C:4]([N:7]2[CH2:12][CH2:11][O:10][CH:9]([CH3:13])[CH2:8]2)=[N:5][N:6]=1.C(O[CH:17]=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])C>>[CH3:13][CH:9]1[CH2:8][N:7]([C:4]2[S:3][C:2]([NH:1][CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N:6][N:5]=2)[CH2:12][CH2:11][O:10]1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 20278758HCID 20278758, compound

Product 1

HCID 13312969HCID 13312969, compound

Procedure

2-amino-5-(2-methyl-morpholino)-1,3,4-thiadiazole (10 g) was reacted with diethyl ethoxymethylene-malonate (11.3 g) at 120° C. for 30 minutes: after cooling the reaction mixture was crystallized from isopropyl ether to give diethyl N-[5-(2-methyl-morpholino)-1,3,4-thiadiazol-2-yl]-aminomethylene-malonate, m.p. 89°-91° C. (16.4 g), which was treated with polyphosphoric acid (6.9 g) and POCl3 (27.15 g) under stirring at 120° C. for 30 minutes.

Workup

  1. temperatureafter cooling the reaction mixture
  2. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-819d08a3c1c54cce8a8421459e4d4361
Source dataset
uspto-grants-1985_06
Patent number
US04522944

Reaction notes

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