Phosphorus oxychloride → Phosphoramidic dichloride, bis(2-chloroethyl)-

HRID 1384049Notes

Reaction equation

HRID 1384049 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][Cl:8].[O:9]=[P:10](Cl)([Cl:12])[Cl:11]>>[Cl:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][Cl:8])[P:10]([Cl:12])([Cl:11])=[O:9]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

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

Procedure

A mixture of bis(2-chloroethyl)amine hydrochloride (5 g) and POCl3 (13 mL) was heated at reflux for 12 hours, during which the mixture became a homogeneous solution. The excess POCl3 was removed by distillation (bp 105° C.), and then 4.93 g of the product was distilled (bp 110-114° C., 0.1 mm Hg). Recrystalliztion from acetone/hexane gave 4.5 g of the product as a colorless solid: mp 54.5-56° C. (lit. 54-56° C., Friedman, O. M., et. al., J. Am. Chem. Soc. 76 (1954):655-658); 1H NMR (CDCl3) δ 3.62-3.68 (m, 2), 3.71-3.77 (m, 6).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours, during which the mixture
  3. customThe excess POCl3 was removed by distillation (bp 105° C.)
  4. distillation4.93 g of the product was distilled (bp 110-114° C., 0.1 mm Hg)

Sources & evidence

ORD record
ord-de13bb204ac744c9a7a922c3103a9730
Source dataset
uspto-grants-2001_07
Patent number
US06258360B1

Reaction notes

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