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4,5-Dihydro-2-(methylthio)thiazole → (4R)-4,5-Dihydro-2-(methylthio)-4-thiazolemethanol

HRID 1957384
Notes
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Reaction equation

HRID 1957384 reaction equation
[C:1](=[O:4])([O-])O.[K+].[CH3:6][S:7][C:8]1[S:9][CH2:10][CH2:11][N:12]=1>>[OH:4][CH2:1][C@@H:11]1[CH2:10][S:9][C:8]([S:7][CH3:6])=[N:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 883244,5-Dihydro-2-(methylthio)thiazoleHCID 516893Potassium Bicarbonate2×

Product 1

HCID 22862349(4R)-4,5-Dihydro-2-(methylthio)-4-thiazolemethanolYield 99.2%

Procedure

To a 73 ml solution of methanol anhydride containing 7.95 g of 3-hydroxyazetidine hydrochloride (5) obtained in the above Example 3, there was added 5.09 g of potassium hydrogencarbonate at a room temperature, and, then, there was added 9.67 g of 2-(methylthio)-1,3-thiazoline dropwise, and, then, the resultant solution was subjected to heating and reflux for 20 hours. After the reaction liquid was left still until it had a room temperature, 3.63 g of potassium hydrogencarbonate was further added, and the liquid was stirred for one hour at the same temperature. After the reaction was over, precipitate was removed by filtration, and the solvent was evaporated in a vacuum, and, to the obtained residue, there was added 100 ml of tetrahydrofuran, and the resulting mixture was stirred for one hour at a room temperature. Insoluble matters were removed by filtration, and the solvent was evaporated in a vacuum, and, then, the residue was subjected to silica gel column chromatography (eluent: chloroform-methanol), and, thus, there was obtained 8.23 g (yield: 71.5%) of 3-hydroxy-1-(1,3-thiazolin-2-yl)azetidine (6) in the form of colorless crystal.

Workup

  1. temperatureto heating
  2. temperaturereflux for 20 hours
  3. customAfter the reaction liquid
  4. waitwas left still until it
  5. customhad a room temperature
  6. customwas removed by filtration
  7. customthe solvent was evaporated in a vacuum
  8. additionto the obtained residue, there was added 100 ml of tetrahydrofuran
  9. stirringthe resulting mixture was stirred for one hour at a room temperature
  10. customInsoluble matters were removed by filtration
  11. customthe solvent was evaporated in a vacuum

Sources & evidence

ORD record
ord-37d7c8607cce4d08884099827dc5568a
Source dataset
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05783703

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes