Diethyl (ethoxymethylene)malonate → 2-(2,2-Dicarbethoxyethenylamino)-4-ethylthiazole

HRID 485136Notes

Reaction equation

HRID 485136 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][CH3:8])[N:6]=1.C(O[CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>>[C:19]([C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][CH3:8])[N:6]=1)([O:21][CH2:22][CH3:23])=[O:20]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 123782054-Ethyl-1,3-thiazol-2-amine

Product 1

HCID 132533622-(2,2-Dicarbethoxyethenylamino)-4-ethylthiazole

Procedure

2-Amino-4-ethylthiazole (20.5 g., 0.16 mole) and diethyl ethoxymethylenemalonate (35 g., 0.17 mole) were combined and heated on a steam bath for 2 hours. 2-(2,2-dicarbethoxyethenylamino)-4-ethylthiazole was obtained as an oil on cooling, and was used directly in the next step. (Rf 0.75 on silica gel thin layer chromatography with chloroform/1% ethanol as eluant.)

Workup

  1. temperatureheated on a steam bath for 2 hours

Sources & evidence

ORD record
ord-ca5f3bd8146845778eab04a679adb7b4
Source dataset
uspto-grants-1985_08
Patent number
US04535081

Reaction notes

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