Phosphorus pentachloride → HCID 54261612, compound

HRID 2227465Notes

Reaction equation

HRID 2227465 reaction equation
[C:1]1([S:7]([N:10]([CH3:22])[NH:11][C:12](=O)[C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:24]>ClCCCl>[C:1]1([S:7]([N:10]([CH3:22])[N:11]=[C:12]([Cl:24])[C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 18473849HCID 18473849, compound

Product 1

HCID 54261612HCID 54261612, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Into a 1 L three necked round bottom flask equipped with a magnetic stirrer and condenser under an atmosphere of nitrogen was added N-benzenesulfonyl-N-methyl-2,6-dichlorobenzoyl hydrazine (35.9 g, 0.10 mol), 1,2-dichloroethane (500 mL), and phosphorus pentachloride (31.2 g, 0.15 mol). The temperature of the mixture was raised to the point of reflux and was allowed to stir for 30 min. The solvent was removed in vacuo and the residue dissolved in methylene chloride and carefully diluted with water. The organic phase was washed with water, brine, dried (Na2SO4) and the solvent removed in vacuo to give an oil which solidified when triturated with ethyl acetate/hexanes mixture to give 36.1 g (95.7% yield) N-benzenesulfonyl-N-methyl-2,6-dichlorobenzhydrazonoyl chloride as a white crystalline solid: mp 103-104° C.; 1H NMR (CDCl3) δ7.9 (m, 2H), 7.4-7.7 (m, 3H), 7.2-7.4 (m, 3H), 3.1 (s, 3H).

Workup

  1. temperatureThe temperature of the mixture was raised to the point
  2. temperatureof reflux
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in methylene chloride
  5. additioncarefully diluted with water
  6. washThe organic phase was washed with water, brine
  7. dry with materialdried (Na2SO4)
  8. customthe solvent removed in vacuo
  9. customto give an oil which
  10. customtriturated with ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-8a6acf2230c54d98b1284cf84dc11b6e
Source dataset
uspto-grants-2002_07
Patent number
US06413997B1

Reaction notes

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