Water → 2-(4-Chlorophenyl)-4-thiazoleacetic acid ethyl ester

HRID 554833Notes

Reaction equation

HRID 554833 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14](=[O:20])[CH2:15][C:16]([CH2:18]Cl)=O)[CH3:12].O>CCO>[CH2:11]([O:13][C:14](=[O:20])[CH2:15][C:16]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[S:7][CH:18]=1)[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 69484Ethyl 4-chloroacetoacetateHCID 27348264-Chlorothiobenzamide

Product 1

HCID 1522972-(4-Chlorophenyl)-4-thiazoleacetic acid ethyl esterYield 89.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 4-chlorothiobenzamide (74.0 g, 431.1 mmol) in EtOH (470 mL) and treat with ethyl-4-chloroacetoacetate (58.0 mL, 70.1 g, 426.0 mmol). Stir the resulting solution mechanically at reflux for 2 h. Cool to room temperature, add water (1000 mL), and extract with Et2O (2000 mL, then 2×500 mL). Combine the organic solutions and wash with brine (950 mL). Concentrate in vacuo to give an oil that solidifies upon standing (121.8 g). Recrystallize the crude material from isopropanol/water to give the title compound (107.3 g, 89% yield). ES/MS m/z (35Cl) 282.1 [M+1]+.

Workup

  1. temperatureat reflux for 2 h
  2. extractionextract with Et2O (2000 mL
  3. washCombine the organic solutions and wash with brine (950 mL)
  4. concentrationConcentrate in vacuo
  5. customto give an oil that
  6. customRecrystallize the crude material from isopropanol/water

Sources & evidence

ORD record
ord-86d83cffa3534fed86af20b7ab455e86
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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