Chloroform → 2-(2,2-Dicarbethoxyethenylamino)-5-ethylthiazole

HRID 905312Notes

Reaction equation

HRID 905312 reaction equation
NC1SC(CC)=CN=1.C(OC=C(C(OCC)=O)C(OCC)=O)C.[C:24]([CH:29]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:30][NH:31][C:32]1[S:33][C:34]([CH2:37][CH3:38])=[CH:35][N:36]=1)([O:26][CH2:27][CH3:28])=[O:25].C(Cl)(Cl)Cl>C(OCC)(=O)C.CCCCCC>[C:24]([C:29]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:30][NH:31][C:32]1[S:33][C:34]([CH2:37][CH3:38])=[CH:35][N:36]=1)([O:26][CH2:27][CH3:28])=[O:25]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6871Diethyl (ethoxymethylene)malonateHCID 127372575-Ethyl-1,3-thiazol-2-amineHCID 20271261HCID 20271261, compound

Product 1

HCID 132533582-(2,2-Dicarbethoxyethenylamino)-5-ethylthiazole

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-ethylthiazole (11.7 g., 91.3 mmoles) and diethyl ethoxymethylenemalonate (21.7 g., 100.43 mmoles) were combined and heated on a steam bath for 45 minutes. 2-(2,2-Dicarbethoxyethylamino)-5-ethylthiazole (27.2 g., Rf 0.6 and 0.7 respectively, on silica gel thin layer chromatography, with chloroform/1% ethanol and with 2:1 hexane:ethyl acetate as eluant) was obtained as an oil by cooling and used directly in the next step.

Workup

  1. temperatureheated on a steam bath for 45 minutes
  2. temperatureby cooling

Sources & evidence

ORD record
ord-f14dd1b660ae4aa4a83a4f83185d3d06
Source dataset
uspto-grants-1983_12
Patent number
US04423048

Reaction notes

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