2-Aminothiazole → Diethyl {[(1,3-thiazol-2-yl)amino]methylidene}propanedioate

HRID 905310Notes

Reaction equation

HRID 905310 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C(O[CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])C>>[C:17]([C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)([O:19][CH2:20][CH3:21])=[O:18]

Participants

3

Reactant 2

HCID 21552-AminothiazoleHCID 6871Diethyl (ethoxymethylene)malonate

Product 1

HCID 13281138Diethyl {[(1,3-thiazol-2-yl)amino]methylidene}propanedioate

Procedure

2-Aminothiazole (10.0 g., 0.10 mole) and diethyl ethoxymethylenemalonate (23.8 g., 0.11 mole) were combined and heated on a steam bath for 1.25 hours. The reaction mixture was cooled and the resulting semisolid recrystallized from hexane to yield purified 2-(2,2-dicarbethoxyethenyl)thiazole (17.2 g. in two crops, Rf 0.6 on silica gel thin layer chromatography with chloroform/1% ethanol as eluant).

Workup

  1. temperatureheated on a steam bath for 1.25 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe resulting semisolid recrystallized from hexane
  4. customto yield
  5. custompurified 2-(2,2-dicarbethoxyethenyl)thiazole (17.2 g. in two crops, Rf 0.6 on silica gel thin layer chromatography with chloroform/1% ethanol as eluant)

Sources & evidence

ORD record
ord-c39287f8be0e48e19007b41c621c512b
Source dataset
uspto-grants-1983_12
Patent number
US04423048

Reaction notes

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