Phenothiazine → Diethyl allylphosphonate

HRID 328543

Reaction equation

HRID 328543 reaction equation
[P:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:2]CC.[CH:11]1[C:24]2NC3C(=CC=CC=3)SC=2C=C[CH:12]=1.C(Cl)C=C>[Co]>[CH2:9]([O:8][P:1]([CH2:24][CH:11]=[CH2:12])(=[O:2])[O:5][CH2:6][CH3:7])[CH3:10]

Participants

5

Reactant 3

HCID 7108PhenothiazineHCID 7850Allyl chlorideHCID 31215Triethyl phosphite

Product 1

HCID 573014Diethyl allylphosphonate

Reagents, catalysts & solvents 1

HCID 104730CobaltCatalyst

Procedure

166 parts of triethyl phosphite are heated for 1 hour to 140° C in a nitrogen atmosphere with 2 parts of highly active Raney cobalt (Ra-Co-Lu). A mixture of 1 part of phenothiazine and 80 parts of allyl chloride is then added dropwise at 140° C. Once the reaction has started, the temperature may be lowered to 120° C. After 5.5 hours, 63 parts of ethyl chloride have distilled off and the mixture is deep blue in colour. Fractional distillation gives 135 parts of allyl phosphonic acid diethyl ester, corresponding to 76% of the theoretical yield.

Workup

  1. additionis then added dropwise at 140° C
  2. custommay be lowered to 120° C
  3. distillation63 parts of ethyl chloride have distilled off
  4. distillationFractional distillation

Sources & evidence

ORD record
ord-d23f6875737846dd9075b4bb91fd9f56
Source dataset
uspto-grants-1977_04
Patent number
US04017564

Linked notes

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