Phosphorus pentachloride → HCID 18981624, compound

HRID 327015Notes

Reaction equation

HRID 327015 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[CH2:7]([P:9]([CH2:15][O:16][S:17]([C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:27])(=[O:19])=[O:18])(=O)[O:10]C(C)C)[CH3:8]>ClCCCl>[CH2:7]([P:9]([Cl:2])([CH2:15][O:16][S:17]([C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:27])(=[O:19])=[O:18])=[O:10])[CH3:8]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachloride2×HCID 53672831HCID 53672831, compound2×

Product 1

HCID 18981624HCID 18981624, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phosphorus pentachloride, 8.32 g, was added in approximately three equal portions over 15 minutes to a mixture at 20° C. of 11.4 g of O-isopropyl P-ethyl[[(2-chloro-6-methylphenyl)-sulfonyloxy]methyl]phosphinate (Compound 119) and 30 ml of 1,2-dichloroethane. Each addition of the phosphorus pentachloride caused a mild exotherm, but the reaction temperature did not exceed 32° C. The reaction slowly cooled to room temperature and was allowed to stir for 72 hours. A 3 ml aliquot of the reaction mixture was concentrated and analyzed by 31P NMR. The 31P NMR indicated that the reaction was complete. The remainder of the reaction mixture was concentrated, 100 ml of toluene was added, the mixture reconcentrated and then high vacuum was pulled on the sample at 55° C. for one hour to yield 10.5 g of the crude desired product.

Workup

  1. customdid not exceed 32° C
  2. customThe reaction
  3. concentrationA 3 ml aliquot of the reaction mixture was concentrated
  4. concentrationThe remainder of the reaction mixture was concentrated
  5. addition100 ml of toluene was added
  6. waithigh vacuum was pulled on the sample at 55° C. for one hour

Sources & evidence

ORD record
ord-a722e7f04a4d4d6da886feabc7804154
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

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