Diisopropylamine → HCID 86744989, compound

HRID 2248425Notes

Reaction equation

HRID 2248425 reaction equation
[Cl-:1].[Cl-].[CH3:3][O:4][P:5]([OH:7])[OH:6].[CH:8]([NH:11][CH:12]([CH3:14])[CH3:13])([CH3:10])[CH3:9]>CCOCC.CCCCC>[CH3:3][O:4][P:5]([OH:7])[OH:6].[Cl-:1].[CH:8]([N-:11][CH:12]([CH3:14])[CH3:13])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 7912DiisopropylamineHCID 131716972HCID 131716972, compound

Product 1

HCID 86744989HCID 86744989, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8003PentaneSolvent2×

Procedure

127 g (0.96 mol) of phosphorous acid methyl ester-dichloride are initially taken in a mixture of 250 ml of absolute ether and 250 ml of absolute pentane, and a solution of 270 ml (1.92 mol) of diisopropylamine in 100 ml of absolute ether and 100 ml of absolute pentane is added dropwise in the course of 2 hours at -15° C., with vigorous stirring and nitrogen blanketing. The reaction mixture is allowed to heat up to room temperature while being stirred, and is then stirred for a further 2 hours. It is then cooled to -15° C. again, and the hydrochloride is removed from the reaction solution by filtration under an inert gas. The filter cake is rinsed with 750 ml of a cold mixture of equal volumes of absolute ether and absolute pentane. The filtrates are combined, and the solvents are removed under a water pump vacuum. The residue is subjected twice to a high-vacuum distillation through an 80 cm Vigreux column. This gives 80 g of a main fraction (boiling point 38 to 41° C. at 0.1 mbar) which, according to 31P-NMR, is composed of 99% of a single substance (δ=185 ppm).

Workup

  1. stirringwhile being stirred
  2. stirringis then stirred for a further 2 hours
  3. temperatureIt is then cooled to -15° C. again
  4. customthe hydrochloride is removed from the reaction solution by filtration under an inert gas
  5. washThe filter cake is rinsed with 750 ml of a cold mixture of equal volumes of absolute ether and absolute pentane
  6. customthe solvents are removed under a water pump vacuum
  7. distillationThe residue is subjected twice to a high-vacuum distillation through an 80 cm Vigreux column

Sources & evidence

ORD record
ord-90c92cb5322c4b67bd1380a180a0e950
Source dataset
uspto-grants-1991_08
Patent number
US05039796

Reaction notes

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