Ethyl thiooxamate → HCID 19375962, compound

HRID 1656408Notes

Reaction equation

HRID 1656408 reaction equation
[NH2:1][C:2](=[S:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[CH2:10][C:11]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([Cl:23])[CH:14]=1)=O>C(O)C>[Cl:23][C:15]1[CH:14]=[C:13]([C:11]2[N:1]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:8][CH:10]=2)[CH:18]=[C:17]([O:19][CH3:20])[C:16]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 2733398Ethyl thiooxamateHCID 19375988HCID 19375988, compound

Product 1

HCID 19375962HCID 19375962, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of ethyl aminothioxoacetate (16.2 g) in ethanol (80 ml), stirred under nitrogen at reflux, was added dropwise over 10 min, a hot solution of 2-bromo-1-(3-chloro-4,5-dimethoxyphenyl)-ethanone (31.9 g) in ethanol (180 ml). The mixture was heated at reflux for 4 h, then cooled to room temperature. The precipitated solid was collected by filtration and dried under vacuum at 60° C. Recrystallisation from ethanol gave ethyl 4-(3-chloro-4,5-dimethoxyphenyl)-thiazole-2-carboxylate as a white solid (21.9 g), m.p. 92°-94° C.

Workup

  1. temperatureat reflux
  2. additionwas added dropwise over 10 min
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 4 h
  5. filtrationThe precipitated solid was collected by filtration
  6. customdried under vacuum at 60° C
  7. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-f3e1577f1ad4440ca40cf6526005650c
Source dataset
uspto-grants-1993_10
Patent number
US05254575

Reaction notes

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