Phosphorus pentachloride → HCID 15169796, compound

HRID 280531Notes

Reaction equation

HRID 280531 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH:9]=[N:10][S:11](=O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:14]>ClC(Cl)C>[Cl:14][C:9]1[C:8]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[S:11][N:10]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachloride2×HCID 70455076HCID 70455076, compound

Product 1

HCID 15169796HCID 15169796, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

The 4-methoxy benzisothiazolone (0.065 mole) was dissolved in 200 mL of dichloroethane and PCl5 (1.05 mole equiv.) was added neat. The reaction was refluxed-monitored by tlc. An additional 0.25 mole equiv. and 2×0.10 mole equiv. of PCl5 was added after 1 hour, 21/2 hours, and 3 hours before the reaction was judged complete by tlc. The reaction was cooled and the solvent and excess reagent removed by house vacuum distillation. The residue was flash chromatographed (30% CH2Cl2 /70% hexane) affording the 3-chloro-4-methoxy-1,2-benzisothiazole in 60% yield.

Workup

  1. custom2 hours, and 3 hours
  2. temperatureThe reaction was cooled
  3. customthe solvent and excess reagent removed by house vacuum distillation
  4. customchromatographed (30% CH2Cl2 /70% hexane)

Sources & evidence

ORD record
ord-56586da03cf04206b42548e6356d8ba5
Source dataset
uspto-grants-1986_05
Patent number
US04590196

Reaction notes

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