Acetic Anhydride → 2-(2-Acetoxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole

HRID 544664Notes

Reaction equation

HRID 544664 reaction equation
[OH:1][CH2:2][CH2:3][S:4][C:5]1[S:6][C:7]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:9]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>>[C:26]([O:1][CH2:2][CH2:3][S:4][C:5]1[S:6][C:7]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[N:9]=1)(=[O:28])[CH3:27]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 132096672-(2-Hydroxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole

Product 1

HCID 204583632-(2-Acetoxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole

Procedure

5.0 g of 2-(2-hydroxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole are suspended in 50 ml of acetic anhydride and, while stirring, the suspension is heated to the boil and refluxed for 15 minutes. The product is concentrated to dryness by evaporation under reduced pressure, two 30 ml portions of xylene are added, with concentration by evaporation being carried out again after each addition to remove traces of acetic anhydride, and the residue is dried under reduced pressure. 2-(2-Acetoxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole is obtained in the form of an oil, Rf =0.33 (silica gel toluene/ethyl acetate 10:1), IR-spectrum: νC=O =1730 cm-1 (CCl4).

Workup

  1. temperaturethe suspension is heated to the boil
  2. temperaturerefluxed for 15 minutes
  3. concentrationThe product is concentrated to dryness by evaporation under reduced pressure, two 30 ml portions of xylene
  4. additionare added, with concentration by evaporation
  5. additionafter each addition
  6. customto remove traces of acetic anhydride
  7. customthe residue is dried under reduced pressure

Sources & evidence

ORD record
ord-e477768b3a92435bbd60403c66f39988
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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