Sodium Carbonate → 4,5-Dimethyl-2-Methylsulphonyloxazole

HRID 613987Notes

Reaction equation

HRID 613987 reaction equation
[CH3:1][C:2]1[N:3]=[C:4](SC)[O:5][C:6]=1[CH3:7].[C:10](=O)([O-])[O-].[Na+].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[S:27]([O-:30])([O-])=[O:28].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[N:3]=[C:4]([S:27]([CH3:10])(=[O:30])=[O:28])[O:5][C:6]=1[CH3:7]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 112520762-Methylthio-4,5-dimethyloxazole

Product 1

HCID 226270084,5-Dimethyl-2-Methylsulphonyloxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

4,5-Dimethyl-2-methylthiooxazole (4.21 g, 0.029 m) in dry chloroform (15 ml) was cooled to 0° C. and anhydrous sodium carbonate (8.0 g, 0.0755 m) added. 88.5% 3-Chloroperbenzoic acid (11.5 g, 0.059 m) in dry chloroform was then added over 45 minutes, and the mixture stirred for a further 45 minutes at 0° C. Solid sodium sulphite (5 g) was then added and the mixture allowed to warm to room temperature. The mixture was then filtered and the filtrate evaporated, the residue being chromatographed on silica using diethyl ether. The resulting solid was recrystallised from ethyl acetate/hexane as the title product, m.p. 42° C.

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe mixture was then filtered
  3. customthe filtrate evaporated
  4. customthe residue being chromatographed on silica
  5. customThe resulting solid was recrystallised from ethyl acetate/hexane as the title product, m.p. 42° C.

Sources & evidence

ORD record
ord-fcd49446998a4b2cac0a6af526439826
Source dataset
uspto-grants-1979_03
Patent number
US04143047

Reaction notes

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