Ethyl 2-chloroacetoacetate → Ethyl 2-(2,4-dichlorophenyl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 1498932

Reaction equation

HRID 1498932 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[S:5].Cl[CH:13]([C:19]([CH3:21])=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]1[S:5][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:19]([CH3:21])[N:6]=1

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 27348222,4-Dichlorobenzenecarbothioamide

Product 1

HCID 58657933Ethyl 2-(2,4-dichlorophenyl)-4-methyl-1,3-thiazole-5-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (10 ml), 2,4-dichlorothiobenzamide (378 mg) was dissolved, and ethyl 2-chloroacetoacetate (302 mg) was added thereto. The mixture was heated under reflux for 25 hours. After the mixture was allowed to cool, the precipitated crystal was separated by filtration, washed with water, and dried to give ethyl 2-(2,4-dichlorophenyl)-4-methylthiazole-5-carboxylate (368 mg, 64%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 25 hours
  3. temperatureto cool
  4. customthe precipitated crystal was separated by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-750a4e1c9298490da065ea5e7c3488a9
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Linked notes

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