Sodium Carbonate → 4-Methyl-2-methylsulphinyloxazole

HRID 613986Notes

Reaction equation

HRID 613986 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([S:7][CH3:8])[O:5][CH:6]=1.C(=O)([O-])[O-:10].[Na+].[Na+].ClC1C=CC=C(C(OO)=O)C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[N:3]=[C:4]([S:7]([CH3:8])=[O:10])[O:5][CH:6]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 213297424-Methyl-2-methylthiooxazole

Product 1

HCID 541594704-Methyl-2-methylsulphinyloxazoleYield 95.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4-Methyl-2-methylthiooxazole (6.06 g, 0.047 m) in dry chloroform (50 ml) was cooled to 0° C. with vigorous stirring and anhydrous sodium carbonate (6.06 g, 0.057 m) added. 96% 3-Chloroperbenzoic acid (8.90 g, 0.0495 m) in dry chloroform (100 ml) was then added dropwise over 45 minutes and the mixture stirred for a further 45 minutes at 0° C. Solid sodium sulphite (2.0 g) was added and the mixture allowed to warm to room temperature. The mixture was then filtered, the filtrate evaporated and the resulting oil was distilled under vacuum to give the title compound as a colourless oil 6.48 g (95%), b.p. (airbath)76° C./0.1 mm.

Workup

  1. stirringthe mixture stirred for a further 45 minutes at 0° C
  2. filtrationThe mixture was then filtered
  3. customthe filtrate evaporated
  4. distillationthe resulting oil was distilled under vacuum

Sources & evidence

ORD record
ord-d7e502c135f748e6b3902d2e5e20be90
Source dataset
uspto-grants-1979_03
Patent number
US04143047

Reaction notes

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