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

HRID 544647
Notes
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Reaction equation

HRID 544647 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+].I[CH2:26][CH2:27][OH:28].Cl>CN(C)P(=O)(N(C)C)N(C)C.CCCCCC>[OH: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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12225IodoethanolHCID 24758Sodium hydrideHCID 132096564,5-Bis-(p-methoxyphenyl)-thiazoline-2-thione

Product 1

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

Reagents, catalysts & solvents 2

HCID 8058
Hexane
Solvent
HCID 12679HexamethylphosphoramideSolvent

Procedure

10 g of 4,5-bis-(p-methoxyphenyl)-thiazoline-2-thione are dissolved in 50 ml of hexamethylphosphoric acid triamide, the solution is cooled to 5° and, while stirring, sodium hydride (1.45 g of a 50% strength suspension in mineral oil, de-oiled with hexane) is added. The mixture is then stirred for 30 minutes at room temperature, 5.22 g of 2-iodoethanol are added dropwise thereto, and the mixture is then stirred for 15 minutes at room temperature and poured into a mixture of 30 ml of 2 N hydrochloric acid and 400 ml of ice-water. After being left to stand for some time the oil which separates crystallises and is taken up in 200 ml of methylene chloride. The solution is dried over magnesium sulphate and concentrated to dryness by evaporation. To crystallise, the residue is triturated with diethyl ether. 2-(2-hydroxyethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole having a melting point of 83°-84° is obtained.

Workup

  1. temperaturethe solution is cooled to 5°
  2. stirringThe mixture is then stirred for 30 minutes at room temperature
  3. stirringthe mixture is then stirred for 15 minutes at room temperature
  4. waitAfter being left
  5. customseparates crystallises
  6. dry with materialThe solution is dried over magnesium sulphate
  7. concentrationconcentrated to dryness by evaporation
  8. customTo crystallise
  9. customthe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-c66691e6d2434365849de80c4fb9ea20
Source dataset
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04451471

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes