Chloroform → 2-[(2,5-dimethylphenyl)chloromethylsulfonyl]pyridine

HRID 2300987Notes

Reaction equation

HRID 2300987 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]([Cl:20])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=1[O-])(=[O:12])=[O:11].P(Cl)(Cl)Cl.C(Cl)(Cl)Cl>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]([Cl:20])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24387Phosphorus trichlorideHCID 12955706HCID 12955706, compound

Product 1

HCID 5012502-[(2,5-dimethylphenyl)chloromethylsulfonyl]pyridineYield 79.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.0 g (0.0064 mole) of 2-[(2,5-dimethylphenyl)-chloromethylsulfonyl]-pyridine N-oxide, 3.5 g (0.026 mole) of PCl3 and 15 ml of chloroform was refluxed for one hour. Addition of ethanol to destroy excess PCl3 and evaporation of the solvents left 2.6 g of crude product. The crude material was recrystallized from ethanol to give 1.5 g (79%) of crystalline material having a melting point of 117-119° C. Infrared and NMR spectra were in agreement with the structure. Analysis calculated for C14H14ClNO2S: C=56.85; H=4.77; N=4.74. Found: C=56.67; H=4.78; N=4.81.

Workup

  1. temperaturewas refluxed for one hour
  2. customto destroy excess
  3. customPCl3 and evaporation of the solvents
  4. waitleft 2.6 g of crude product
  5. customThe crude material was recrystallized from ethanol

Sources & evidence

ORD record
ord-5eeb43ccef2042c8bbbe28522298231a
Source dataset
uspto-grants-2002_12
Patent number
US06498254B1

Reaction notes

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