Octane → Phosphoramidic dichloride, bis(2-chloroethyl)-

HRID 267593

Reaction equation

HRID 267593 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][Cl:8].[P:9](Cl)([Cl:12])([Cl:11])=[O:10].NC1C=CC(S(C=CC#N)(=O)=O)=CC=1.CCCCCCCC>CC(C)=O.N1C=CC=CC=1>[Cl:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][Cl:8])[P:9]([Cl:12])([Cl:11])=[O:10]

Participants

7

Reactant 4

HCID 356OctaneHCID 24813Phosphorus oxychlorideHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 545613262-Cyanovinyl 4-aminophenyl sulfone

Product 1

HCID 96271Phosphoramidic dichloride, bis(2-chloroethyl)-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 1049PyridineSolvent

Procedure

Di-(2-chloroethyl)amidophosphorodichloridate is prepared according to H. Brintzinger et al in Chemische Berichte 82, 389-99 (1949) from bis-(2-chloroethyl)amine hydrochloride and phosphoryl chloride in the presence of pyridine. 0.03 mol (7.8 g) of this material is dissolved in 100 ml of acetone and added to an acetone solution of 0.03 mole (6.3 g) of 2-cyanovinyl 4-aminophenyl sulfone. To the stirred mixture is added in 2-3 portions a 10% solution of 1,4-diazabicyclo[2.2.2.]octane in acetone. After a few minutes a yellow slurry forms which is stirred at room temperature for 30 minutes. After filtration to remove the amine hydrochlorides the filtrate is reduced to about half its volume by evaporation and then mixed with chloroform, washed with water and worked up. The light yellow solid is di-(2-chloroethyl)amido-di-4-(2-cyanoethenesulfonylanilido)phosphine oxide: ##SPC57##

Workup

  1. filtrationAfter filtration
  2. customto remove the amine hydrochlorides the filtrate
  3. customis reduced to about half its volume by evaporation
  4. additionmixed with chloroform
  5. washwashed with water

Sources & evidence

ORD record
ord-985e4505f57f40b8bce98de6f210dac8
Source dataset
uspto-grants-1976_03
Patent number
US03943154

Linked notes

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