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

HRID 1406839Notes

Reaction equation

HRID 1406839 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.Cl[CH:12]([C:18]([CH3:20])=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:7][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:18]([CH3:20])[N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 27593444-Hydroxythiobenzamide

Product 1

HCID 135509402Ethyl 2-(4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

Procedure

A mixture of 4-hydroxy thiobenzamide (100 g, 0.653 mol) and ethyl 2-chloroacetoacetate (118.3 g, 0.719 mol) in denatured spirit (DNS) (500 mL) was heated at about 60° C. to 65° C. for about 2.5 hours. The reaction mixture was cooled to about 0° C. to 5° C. and stirred for about 1 hour at the same temperature. The solid obtained was filtered, washed with denatured spirit and dried to obtain the title compound. (Yield: 156 g, 90.7%)

Workup

  1. temperaturewas heated at about 60° C. to 65° C. for about 2.5 hours
  2. temperatureThe reaction mixture was cooled to about 0° C. to 5° C.
  3. customThe solid obtained
  4. filtrationwas filtered
  5. washwashed with denatured spirit
  6. customdried

Sources & evidence

ORD record
ord-70bf0bb5310d4795a214c3354d564430
Source dataset
uspto-grants-2014_12
Patent number
US08916713B2

Reaction notes

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