Thiophosphoryl chloride → HCID 13545839, compound

HRID 371257Notes

Reaction equation

HRID 371257 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[P:6](Cl)([Cl:9])([Cl:8])=[S:7]>CCOCC>[Cl:8][P:6]([Cl:9])([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[S:7]

Participants

4

Reactant 2

HCID 19883Thiophosphoryl chlorideHCID 31268Pyrrolidine

Product 1

HCID 13545839HCID 13545839, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 43.4 mL (0.52 mol) of pyrrolidine in 50 mL of ether was added dropwise to a stirred solution of 116 mL (1.04 mol) of thiophosphoryl chloride in 200 mL of ether at 0° C. (ice bath) under an argon atmosphere. After the addition was completed, the resultant slurry was slowly warmed to room temperature overnight. A trace of pyrrolidinium hydrochloride was removed by filtration and the filtrate was concentrated under vacuum to provide 84.5 g of a clear oil. A portion of this oil (40 g) was distilled at 80° C. (0.25 mm) to provide 18.1 g of the desired dichloride as a clear oil.

Workup

  1. additionAfter the addition
  2. customA trace of pyrrolidinium hydrochloride was removed by filtration
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-f541ef3cc3244120ad96c0feeb6caf8b
Source dataset
uspto-grants-1985_07
Patent number
US04530714

Reaction notes

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