Acetic Acid → 3-(2-(4-Isopropyl-2-thiazolyl))ethenylbenzoic acid

HRID 1650683Notes

Reaction equation

HRID 1650683 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]2[S:12][CH:13]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=2)[CH:6]=CC=1)#N.O.[C:20]([OH:23])(=[O:22])[CH3:21]>Cl>[CH:16]([C:14]1[N:15]=[C:11]([CH:10]=[CH:9][C:5]2[CH:6]=[C:21]([CH:1]=[CH:3][CH:4]=2)[C:20]([OH:23])=[O:22])[S:12][CH:13]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 537541442-(2-(3-Cyanophenyl)ethenyl)-4-isopropylthiazole

Product 1

HCID 537563913-(2-(4-Isopropyl-2-thiazolyl))ethenylbenzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

2-(2-(3-Cyanophenyl)ethenyl)-4-isopropylthiazole prepared in Synthetic Example (2.54 g, 10.0 mmol) was dissolved in a mixed solvent of acetic acid (5 ml) and concentrated hydrochloric acid (10 ml) and the resulting mixture was heated under stirring at 100° C. for 4 hours. After water was added, the reaction mixture was extracted with ethyl acetate and dried. The solvent was distilled out to afford the indicated compound (2.51 g) with a yield of 92%.

Workup

  1. temperaturethe resulting mixture was heated
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. customdried
  4. distillationThe solvent was distilled out

Sources & evidence

ORD record
ord-95717dc694a84d41b10adb14086e4e04
Source dataset
uspto-grants-1990_05
Patent number
US04925861

Reaction notes

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