Sodium Hydroxide → 2-(Dioctylphosphoryl)-N,N-dimethylacetamide

HRID 1649952Notes

Reaction equation

HRID 1649952 reaction equation
[CH3:1][N:2]([CH3:7])[C:3](=[O:6])[CH2:4]Cl.[CH2:8]([PH:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)Cl>[CH3:1][N:2]([CH3:7])[C:3]([CH2:4][P:16](=[O:25])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:6]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 758862-chloro-N,N-dimethylacetamideHCID 178443876HCID 178443876, compound

Product 1

HCID 128652412-(Dioctylphosphoryl)-N,N-dimethylacetamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a 500 ml, three-necked, round-bottom flask equipped with a thermowell, a mechanical stirrer, a condenser and a septum, was placed a solution of 13.4 g (0.11 mole) of N,N-dimethylchloroacetamide, 27.4 g (0.10 mole) of di(n-octyl)phosphine oxide, and 1.0 g of Adogen 464 in 150 ml of methylene chloride along with 100 ml of 50% sodium hydroxide solution. The solution was stirred at 300 rpm under a gentle reflux until GLC analysis of removed aliquots (2 hours) indicated the consumption of the starting materials. The aqueous layer was extracted with 50 ml of pentane and the combined organic layers were washed with three 50 ml portions of water followed by one 50 ml portion of saturated sodium chloride solution. After drying over anhydrous potassium carbonate, and filtering, the filtrate was evaporated in vacuo (80° C.; 2mm Hg) to yield 29.5 g of an amber oil which was 77% pure by GLC. Upon cooling, the oil crystallized. Recrystallization from pentane afforded a colorless hygroscopic solid which was chromatographically pure, Mp 38.5-40.5. Analytical data obtained for this product is summarized in Table I.

Workup

  1. customInto a 500 ml, three-necked, round-bottom flask equipped with a thermowell, a mechanical stirrer, a condenser
  2. temperaturea gentle reflux until GLC analysis of removed aliquots (2 hours)
  3. customthe consumption of the starting materials
  4. extractionThe aqueous layer was extracted with 50 ml of pentane
  5. washthe combined organic layers were washed with three 50 ml portions of water
  6. dry with materialAfter drying over anhydrous potassium carbonate
  7. filtrationfiltering
  8. customthe filtrate was evaporated in vacuo (80° C.; 2mm Hg)

Sources & evidence

ORD record
ord-615653b4bd0d4209b1aea78fbe566b80
Source dataset
uspto-grants-1990_05
Patent number
US04922012

Reaction notes

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