Dimethyl Sulfate → 2-Methylthio-4,5-dimethyloxazole

HRID 613985Notes

Reaction equation

HRID 613985 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[S:8])[O:5][C:6]=1[CH3:7].S(OC)(O[CH3:13])(=O)=O>[OH-].[Na+]>[CH3:1][C:2]1[N:3]=[C:4]([S:8][CH3:13])[O:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 3036316Dimethyl-1,3-oxazole-2-thiol

Product 1

HCID 112520762-Methylthio-4,5-dimethyloxazoleYield 81.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4,5-Dimethyl-2(3H)-oxazolethione [Bull. Soc. Chim. Belg. 70, 745, (1961)] (37.5 g, 0.29 m) in 2N aqueous sodium hydroxide (150 ml) was stirred at room temperature during the dropwise addition of dimethyl sulphate (40.0 g, 0.317 m). The mixture was stirred for 4 hours at room temperature and then warmed to 50° C, cooled, and the aqueous phase extracted with diethyl ether. Evaporation of the solvent and distillation of the residue under reduced pressure gave 33.85 g (81%) of the title product as a pale yellow oil, b.p. 82° C./13 mm.

Workup

  1. temperaturewarmed to 50° C
  2. temperaturecooled
  3. extractionthe aqueous phase extracted with diethyl ether
  4. customEvaporation of the solvent and distillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-f248384fdea04670a9dd9e247d7049cd
Source dataset
uspto-grants-1979_03
Patent number
US04143047

Reaction notes

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