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

HRID 544657Notes

Reaction equation

HRID 544657 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[S:12][C:11](=[S:22])[N:10]=2)=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:26][CH2:27][CH2:28][OH:29].Cl>CN(C)P(=O)(N(C)C)N(C)C>[OH:29][CH2:28][CH2:27][CH2:26][S:22][C:11]1[S:12][C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 123083-Bromo-1-propanolHCID 24758Sodium hydrideHCID 132096564,5-Bis-(p-methoxyphenyl)-thiazoline-2-thione

Product 1

HCID 204583792-(3-Hydroxypropylthio)-4,5-bis-(p-methoxyphenyl)-thiazole

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6eb20d3ccfd54dcdbcf5e9f5fd9e2da4
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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