Triethyl phosphite → Diethylphosphonoacetylurea

HRID 1578464Notes

Reaction equation

HRID 1578464 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]([NH2:8])=[O:7])=[O:4].[P:9]([O:16]CC)([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]>>[CH2:11]([O:10][P:9]([CH2:2][C:3]([NH:5][C:6]([NH2:8])=[O:7])=[O:4])([O:13][CH2:14][CH3:15])=[O:16])[CH3:12]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 78516(2-Chloroacetyl)urea2×

Product 1

HCID 54436389Diethylphosphonoacetylurea

Procedure

While stirring, 682 gm (5 mol) of chloroacetylurea were added portionwise to 831 gm (5 mol) of triethyl phosphite at a temperature of 135°C to 150°C. Each time, the addition of the next portion was delayed until the violent gas evolution had abated. After the last portion of chloracetylurea had been added, the stirring was continued at 150°C until the evolution of gas was terminated. Small quantities of a volatile substance distilled off when the reaction mixture was heated on the water bath under the vacuum generated by an oil pump. The reaction mixture solidified upon cooling. The pure diethylphosphonoacetylurea was obtained from the crude product by recrystallization from isopropanol or acetone and proved to be a water-soluble product having a melting point of 120°C. The yield of crude product was 1120 gm (94% of the theory).

Workup

  1. additionEach time, the addition of the next portion
  2. customwas continued at 150°C until the evolution of gas
  3. customwas terminated
  4. distillationSmall quantities of a volatile substance distilled off when the reaction mixture
  5. temperaturewas heated on the water bath under the vacuum
  6. temperatureupon cooling

Sources & evidence

ORD record
ord-903c41f0dada49969a581bd14d93c753
Source dataset
uspto-grants-1976_02
Patent number
US03937612

Reaction notes

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