Nitrogen → HCID 86737607, compound

HRID 127872Notes

Reaction equation

C(Cl)([Cl:3])=O.[CH2:5]([O:7][P:8]([CH2:13][CH2:14][CH3:15])(=[O:12])[O:9]CC)[CH3:6].N#N>>[Cl-:3].[CH2:5]([O:7][P:8]([CH2:13][CH2:14][CH3:15])(=[O:9])[OH:12])[CH3:6]

Participants

Reactant 3

HCID 947Nitrogen

HCID 6371Phosgene

HCID 140428Diethyl propanephosphonate

Product 1

HCID 86737607HCID 86737607, compound

Procedure

200 g of phosgene were passed into 1 mole of propane-phosphonic acid diethyl ester at 70°-80° C. The mixture was stirred at 70°-80° C. for 1 hour and a dry N2 stream was passed through the reaction mixture overnight at 50° C. The mixture was completely degassed at 50° C. under a waterpump vacuum in a Rotavapor and crude propanephosphonic acid ethyl ester-chloride was obtained. This was rendered basic with absolute pyridine, dissolved in 300 ml of toluene and reacted with a mixture of 1.1 moles of pyridine and 1 mole of allyl alcohol at 20°-30° C. The mixture was allowed to after-react at 80° C. for 2 hours. The solution which was separated off from the hydrochloride by filtration was concentrated and distilled.

Workup

customwas passed through the reaction mixture overnight at 50° C
customThe mixture was completely degassed at 50° C. under a waterpump vacuum in a Rotavapor

Sources & evidence

ORD record: ord-73930a9416d14d09a65994e74e906bb9
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04257987

Reaction notes

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