Hydrochloric Acid → HCID 13902891, compound

HRID 1646088Notes

Reaction equation

HRID 1646088 reaction equation
[CH:1]([P:4]1(=[O:12])[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[CH2:6][O:5]1)=[C:2]=[CH2:3].[OH2:13].NN.Cl>C(#N)C>[CH2:1]([P:4]1(=[O:12])[O:5][CH2:6][C:7]([CH3:10])([CH3:11])[CH2:8][O:9]1)[C:2]([CH3:3])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 114128111,3,2-Dioxaphosphorinane, 5,5-dimethyl-2-(1,2-propadienyl)-, 2-oxide

Product 1

HCID 13902891HCID 13902891, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.69 g (3.7 mmol) of 2-allenyl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane (II) was dissolved in 3 ml of acetonitrile, and 0.22 g (4.4 mmol) of hydrazine monohydrate was added thereto. The mixture was left for 30 minutes at room temperature. Then, 4.8 g of 10% by weight hydrochloric acid was added thereto and stirred for one hour. The solvent was distilled off to about one-half its initial volume under reduced pressure and the reaction mixture diluted with 30 ml of 20% by weight sodium chloride aqueous solution, was extracted 2 times with 40 ml of chloroform. The chloroform layers were combined and dried over anhydrous sodium sulfate, followed by filtration. The solvent was distilled off to obtain 0.75 g (yield: about quantitative amount) of the desired product of 2-acetonyl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane (IV) as colorless solid.

Workup

  1. distillationThe solvent was distilled off to about one-half its initial volume under reduced pressure
  2. additionthe reaction mixture diluted with 30 ml of 20% by weight sodium chloride aqueous solution
  3. extractionwas extracted 2 times with 40 ml of chloroform
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfollowed by filtration
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-12321f4c850e4bbd867e685f9813b144
Source dataset
uspto-grants-1993_01
Patent number
US05177237

Reaction notes

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