Diethyl (ethoxymethylene)malonate → HCID 20271239, compound

HRID 905311Notes

Reaction equation

HRID 905311 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1.C(O[CH:11]=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])C>>[C:18]([C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][NH:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1)([O:20][CH2:21][CH3:22])=[O:19]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 3517702-Amino-5-methylthiazole

Product 1

HCID 20271239HCID 20271239, compoundYield 82.7%

Procedure

2-Amino-5-methylthiazole (6.85 g., 60 mmoles) and diethyl ethoxymethylenemalonate (14.3 g., 66 mmoles) were heated on a steam bath for 1 hour. The reaction mixture was cooled and the product precipitated by the addition of approximately 75 ml. of hexane. Purified 2-(2,2-dicarbethoxyethenylamino)-5-methylthiazole (14.1 g. in two crops, Rf 0.55-0.65 on silica gel thin layer chromatography with chloroform/1% ethanol as eluant) was obtained by recrystallization from hexane.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe product precipitated by the addition of approximately 75 ml

Sources & evidence

ORD record
ord-3afd233bd1a84929b887fc7fb63f0844
Source dataset
uspto-grants-1983_12
Patent number
US04423048

Reaction notes

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