Triethylamine → Bis-pyrrolidinochlorophosphine oxide

HRID 1282712Notes

Reaction equation

HRID 1282712 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([N:8](CC)[CH2:9][CH3:10])[CH3:7].[O:13]=[P:14](Cl)(Cl)[Cl:15].O=P(Cl)(Cl)Cl.C1C=CC=CC=1>C1C=CC=CC=1>[N:1]1([P:14](=[O:13])([N:8]2[CH2:9][CH2:10][CH2:7][CH2:6]2)[Cl:15])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 31268PyrrolidineHCID 86733772HCID 86733772, compound

Product 1

HCID 305985Bis-pyrrolidinochlorophosphine oxide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The bis-pyrrolidinochlorophosphine oxide was prepared as follows: 56.8 g (0.8 mole) pyrrolidine, 80.8 g (0.8 mole) triethylamine and 300 ml dry benzene were charged into a 1 liter three-necked flask equipped with a stirrer, condenser and dropping funnel. A solution of POCl3 in 70 mls dry benzene was added dropwise under a stream of dry nitrogen. The reaction was exothermic. On complete addition of the POCl3 /benzene solution, the reaction mixture was stirred for 11/2 hours at room temperature. The precipitated triethylamine hydrochloride was filtered off and the filtrate evaporated using a rotary evaporator under reduced pressure (60 mm). The product was fractionally distilled under reduced pressure (0.3 - 0.5 mm) and the fraction distilling between 138°-140° collected. This fraction was identified as ##EQU59##

Workup

  1. customequipped with a stirrer, condenser
  2. filtrationThe precipitated triethylamine hydrochloride was filtered off
  3. customthe filtrate evaporated
  4. customa rotary evaporator under reduced pressure (60 mm)
  5. distillationThe product was fractionally distilled under reduced pressure (0.3 - 0.5 mm)
  6. distillationthe fraction distilling between 138°-140°
  7. customcollected

Sources & evidence

ORD record
ord-21b9dcc131a148a6b238b031287873aa
Source dataset
uspto-grants-1976_08
Patent number
US03972866

Reaction notes

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