2-Chloroethyl isocyanate → alpha-[N-(2-chloroethyl)ureido]benzylphosphonic acid diethyl ester

HRID 1285324Notes

Reaction equation

HRID 1285324 reaction equation
[CH2:1]([O:3][P:4]([CH:9](N)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[Cl:17][CH2:18][CH2:19][N:20]=[C:21]=[O:22].[NH2:23]P(=O)([O-])[O-]>C(Cl)(Cl)Cl>[CH2:6]([O:5][P:4]([CH:9]([N:20]([CH2:19][CH2:18][Cl:17])[C:21]([NH2:23])=[O:22])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

5

Reactant 3

HCID 160352-Chloroethyl isocyanateHCID 211207Phosphoramidic acid, ion(2-)HCID 419299Diethyl amino(phenyl)methylphosphonate

Product 1

HCID 53798997alpha-[N-(2-chloroethyl)ureido]benzylphosphonic acid diethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 0.05 mol of α-aminobenzylphosphonic acid diethyl ester in 30 ml of chloroform is cooled to 0° C. in an ice-bath and then a large excess (0.06 mol) of β-chloroethyl isocyanate is added. The temperature of the reaction is then maintained at 10° C. while continuing stirring until the reaction is complete. (Examination by thin layer chromatography is used to ascertain that the starting aminophosphonate has disappeared completely. After evaporation of the solvent under reduced pressure, the crystalline residue is taken up in ether and filtered, yielding 14.8 g of crystals. Yield: 85%; m.p.=82° C.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. filtrationfiltered

Sources & evidence

ORD record
ord-0cf852b59ea6435d8966c57c256c5a66
Source dataset
uspto-grants-1986_01
Patent number
US04567169

Reaction notes

Loading…