Sodium Hydroxide → [3-[2-(4,5-Diphenyl-2-thiazolyl)ethyl)phenoxy]acetic acid

HRID 1461756Notes

Reaction equation

HRID 1461756 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([O:27]C)=[O:26])[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([OH:27])=[O:26])[S:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10477744Methyl [3-[2-(4,5-diphenyl-2-thiazolyl)ethyl]phenoxy]acetate

Product 1

HCID 15006905[3-[2-(4,5-Diphenyl-2-thiazolyl)ethyl)phenoxy]acetic acidYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl [3-[2-(4,5-diphenyl-2-thiazolyl)ethyl]phenoxy]acetate (2.70 g, 6mmol), 5N NaOH solution (3.77mL, 18mmol) and methanol (40 mL) was heated to reflux on a steam bath. After 20 minutes, the mixture was cooled, the methanol removed and the residue diluted with water and 2N HCl solution. The precipitate was filtered off, washed with water and dried in air. Recrystallization from a mixture of CH2Cl2 and hexanes provide [3-[2-(4,5-diphenyl-2-thiazolyl)ethyl)phenoxy]acetic acid (1.97 g, 75%), mp 118°-120° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux on a steam bath
  3. temperaturethe mixture was cooled
  4. customthe methanol removed
  5. additionthe residue diluted with water and 2N HCl solution
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried in air
  9. customRecrystallization
  10. additionfrom a mixture of CH2Cl2 and hexanes

Sources & evidence

ORD record
ord-b2f6f0cd736649ea822c3377408cd6ad
Source dataset
uspto-grants-1991_12
Patent number
US05077305

Reaction notes

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