Water → Ethyl 2-(4-isopropoxy-3-nitrophenyl)-4-methyl-5-thiazolecarboxylate

HRID 977098Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+].[CH:28](Br)([CH3:30])[CH3:29].O>CN(C)C=O>[CH:28]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 70 °C

Procedure

200 mg of Ethyl 2-(4-hydroxy-3-nitrophenyl)-4-methyl-5-thiazolecarboxylate prepared in (1) was dissolved in 3 ml of N,N-dimethylformamide, 540 mg of anhydrous potassium carbonate and 440 mg of isopropyl bromide were added thereto, and the mixture was heated at 70° C. for 18 hours. After the reaction mixture was cooled, 20 ml of water was added thereto. The mixture was extracted twice with 30 ml of ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and the solvent was removed by distillation. The resulting crystal was recrystallized from ethanol to give 172 mg of ethyl 2-(4-isopropoxy-3-nitrophenyl)-4-methyl-5-thiazolecarboxylate. This product was hydrolyzed by a conventional process, and the resulting crystal was recrystallized from a 80% aqueous ethanol solution to give 135 mg of 2-(4-isopropoxy-3-nitrophenyl)-4-methyl-5-thiazolecarboxylic acid (yield:

Workup

temperatureAfter the reaction mixture was cooled
extractionThe mixture was extracted twice with 30 ml of ethyl acetate
washThe organic layer was washed with a saturated aqueous sodium chloride solution
customthe solvent was removed by distillation
customThe resulting crystal was recrystallized from ethanol

Sources & evidence

ORD record: ord-cbc2e052743c4c50a8231537e2962835
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05614520

Reaction notes

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