Tetrabutylammonium Hydroxide → 2-Vinylthio-4,5-bis-(p-methoxyphenyl)-thiazole

HRID 544669Notes

Reaction equation

HRID 544669 reaction equation
Br[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.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.O>[CH: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:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[N:9]=1)=[CH2:2]

Participants

5

Reactant 2

HCID 2723671Tetrabutylammonium HydroxideHCID 204583302-(2-Bromoethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole

Product 1

HCID 204583472-Vinylthio-4,5-bis-(p-methoxyphenyl)-thiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

0.8 g of 2-(2-bromoethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole are dissolved in 20 ml of toluene. 2 ml of a 30% strength solution of tetrabutylammonium hydroxide in water are added and the mixture is heated under reflux for 2 hours while stirring vigorously. The mixture is then allowed to cool, the organic phase is separated off, washed twice with 10 ml of water each time, dried over sodium sulphate and concentrated to dryness by evaporation. The crude product is purified by chromatography over a silica gel column with toluene/ethyl acetate (10:1) as eluant. The fractions that according to the thin layer chromatogram contain 2-vinylthio-4,5-bis-(p-methoxyphenyl)-thiazole are concentrated by evaporation and dried to constant weight. 2-Vinylthio-4,5-bis-(p-methoxyphenyl)-thiazole is obtained in the form of a pale yellow oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. customthe organic phase is separated off
  5. washwashed twice with 10 ml of water each time
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated to dryness by evaporation
  8. customThe crude product is purified by chromatography over a silica gel column with toluene/ethyl acetate (10:1) as eluant
  9. concentrationare concentrated by evaporation
  10. customdried to constant weight

Sources & evidence

ORD record
ord-eea933dc5ca04b2d8539151a8cd9ee0a
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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