Water → HCID 19965153, compound
Reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(=[S:3])[NH2:2].Cl[CH:14]([C:20]([CH3:22])=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16].O>O1CCOCC1>[C:7]([C:6]1[CH:5]=[C:4]([C:1]2[S:3][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]([CH3:22])[N:2]=2)[CH:12]=[CH:11][CH:10]=1)([OH:9])=[O:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
720 mg of 3-Thiocarbamoylbenzoic acid was suspended in 10 ml of dioxane, 720 mg of ethyl 2-chloroacetoacetate was added thereto, and the mixture was heated at 90° C. for 18 hours. After the reaction mixture was cooled, the resulting crystal was collected from the suspension by filtration and recrystallized from 20 ml of ethanol and a small amount of water to give 735 mg of ethyl 2-(3-carboxyphenyl)-4-methyl-5-thiazolecarboxylate (yield: 63%). 290 mg of the crystal was dissolved in 5 ml of 1N sodium hydroxide, and the mixture was heated at 60° C. for one hour. After the completion of the reaction, the reaction mixture was neutralized with 1N hydrochloric acid. The resulting crystal was collected by filtration and recrystallized from a 80% aqueous ethanol solution to give 258 mg of 2-(3-carboxyphenyl)-4-methyl-5-thiazolecarboxylic acid (yield: 83%).
Workup
- temperatureAfter the reaction mixture was cooled
- filtrationthe resulting crystal was collected from the suspension by filtration
- customrecrystallized from 20 ml of ethanol
Sources & evidence
- ORD record
- ord-3546c693adec46ee8e50e7c9809212fa
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05614520
Reaction notes
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