Hydrochloric Acid → 2-(3-Hydroxypropylthio)-4,5-bis-(p-methoxyphenyl)-thiazole

5.0 g of 4,5-bis-(p-methoxyphenyl)-thiazoline-2-thione are dissolved in 50 ml of hexamethylphosphoric acid triamide under nitrogen at 45°, 0.73 g of 50% strength sodium hydride suspension (in mineral oil, de-oiled with hexane) is added in portions and the mixture is stirred at room temperature for 1 hour. 2.22 g of 3-bromopropanol are then added dropwise. The mixture is then stirred at room temperature for 90 minutes, poured into a mixture of 400 ml of ice-water and 20 ml of 2 N hydrochloric acid, extracted by stirring twice with 100 ml of ethyl acetate each time, washed twice with 100 ml of water each time, dried over sodium sulphate and concentrated by evaporation under reduced pressure. The oily crude product is dissolved in 30 ml of toluene, and chromatographed over a column of 30 g of silica gel with toluene as eluant. The 800-1200 ml fractions are combined, concentrated to dryness by evaporation and dried for 3 hours at 0.01 mbar. Analytically pure 2-(3-hydroxypropylthio)-4,5-bis-(p-methoxyphenyl)-thiazole is obtained in the form of a pale yellow oil, Rf value 0.25 (silica gel thin layer/toluene:ethyl acetate 3:1).

1. stirringThe mixture is then stirred at room temperature for 90 minutes
2. extractionextracted
3. stirringby stirring twice with 100 ml of ethyl acetate each time
4. washwashed twice with 100 ml of water each time
5. dry with materialdried over sodium sulphate
6. concentrationconcentrated by evaporation under reduced pressure
7. dissolutionThe oily crude product is dissolved in 30 ml of toluene
8. customchromatographed over a column of 30 g of silica gel with toluene as eluant
9. concentrationconcentrated to dryness by evaporation
10. customdried for 3 hours at 0.01 mbar

ORD-Eintrag

ord-6eb20d3ccfd54dcdbcf5e9f5fd9e2da4

Quelldatensatz

uspto-grants-1984_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04451471