Dimethyl Sulfoxide → HCID 178503318, compound

HRID 1507638Notes

Reaction equation

HRID 1507638 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([O-:13])[O+:10]=[N:9]2)=[CH:4][CH:3]=1.C(Cl)(=O)C.[CH3:18][S:19](C)=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([S:19][CH3:18])=[C:11]([O-:13])[O+:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 6367Acetyl chlorideHCID 178516722HCID 178516722, compound

Product 1

HCID 178503318HCID 178503318, compound

Procedure

Using the procedure of Masada and Okutani (Tetrahedron 30, 409-414 (1974)) the crude 3-(4-fluorophenyl)-3H-1,2,3-oxadiazol-1-ium-5-olate (1.95 g, 10.82 mmol) was dissolved in anhydrous DMSO (27 mL) and cooled in ice. Acetyl chloride (2.0 g, 25.5 mmol) was added dropwise. The reaction mixture was allowed to come to room temperature. After stiffing overnight, the mixture was partitioned between ether and saturated NaHCO3 solution. The organic layer was washed several times with water, dried and evaporated to dryness to afford 3-(4-fluorophenyl)-4-(methylthio)-3H-1,2,3-oxadiazol-1-ium-5-olate.

Workup

  1. temperaturecooled in ice
  2. customto come to room temperature
  3. customthe mixture was partitioned between ether and saturated NaHCO3 solution
  4. washThe organic layer was washed several times with water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-c4845eaa01a24816838795f5f580cbc2
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

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