Phosphorus pentachloride → (2-Methyl-1,3-thiazol-4-yl)methanesulfonyl chloride

HRID 424886Notes

Reaction equation

HRID 424886 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8]([O-:11])(=O)=[O:9])[N:6]=1.[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:14]>P(Cl)(Cl)(Cl)=O>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8]([Cl:14])(=[O:11])=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 59464713Sodium (2-methylthiazol-4-yl)methanesulfonate

Product 1

HCID 59464691(2-Methyl-1,3-thiazol-4-yl)methanesulfonyl chlorideYield 27%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium (2-methylthiazol-4-yl)methanesulfonate (357 mg, 1.66 mmol) is dissolved in phosphorous oxychloride (6 mL) and is treated with phosphorous pentachloride (345 mg, 1.66 mmol). The reaction mixture is stirred at 50° C. for 3 hours, then allowed to cool to room temperature. The solvent is removed under reduced pressure and the residue is re-dissolved in CH2Cl2 (40 mL) and is washed with sat. NaHCO3 and brine. The organic layer is dried over MgSO4, filtered, and the solvent removed in vacuo to afford 0.095 g of the desired product as a brown oil. LC/MS ESI+211 (M+1). Intermediates are obtained in sufficient purity to be carried forward according to Scheme IX without the need for further purification.

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent is removed under reduced pressure
  3. dissolutionthe residue is re-dissolved in CH2Cl2 (40 mL)
  4. washis washed with sat. NaHCO3 and brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ed1b3b7216774b8096ed321c366770e0
Source dataset
uspto-grants-2012_01
Patent number
US08106078B2

Reaction notes

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