1-(p-Acetamidophenyl)-3-(2-chloroethyl) urea → N-[4-(2-Oxoimidazolidin-1-yl)phenyl]acetamide

HRID 979886Notes

Reaction equation

HRID 979886 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH2:16]Cl)=[O:13])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C[O-].[Na+]>CN(C)C=O.CO>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][C:12]2=[O:13])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 2866861-(p-Acetamidophenyl)-3-(2-chloroethyl) ureaHCID 10942334Sodium Methoxide

Product 1

HCID 13755487N-[4-(2-Oxoimidazolidin-1-yl)phenyl]acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1600 g of 1-(p-acetamidophenyl)-3-(2-chloroethyl) urea in 7200 ml of dimethylformamide is stirred at room temperature under an atmosphere of nitrogen. To the resulting solution is added a solution of 400 g of sodium methoxide in 2000 ml of methyl alcohol (anhydrous) in a thin stream over a 90-minute period. The temperature rises during the addition. The reaction mixture is stirred for an additional 20 minutes and then heated to 70°-75° and kept at this temperature for 1 hour. The reaction mixture is then allowed to cool slowly to 32° over a period of about 3 hours with stirring; 5000 ml of ice-water is then added rapidly. Stirring at room temperature is continued for 4 hours and the mixture is allowed to stand at room temperature overnight. The solid is filtered off and washed with 3000 ml of water and air-dried for about 2 days at room temperature to give 1-(p-acetamidophenyl)-2-imidazolidinone, m.p. 270°-273°.

Workup

  1. additionThe temperature rises during the addition
  2. stirringThe reaction mixture is stirred for an additional 20 minutes
  3. temperatureheated to 70°-75°
  4. temperatureto cool slowly to 32° over a period of about 3 hours
  5. stirringwith stirring
  6. stirringStirring at room temperature
  7. waitis continued for 4 hours
  8. waitto stand at room temperature overnight
  9. filtrationThe solid is filtered off
  10. washwashed with 3000 ml of water
  11. customair-dried for about 2 days at room temperature

Sources & evidence

ORD record
ord-e073af8438ba4b66908c02f8a9c3a96f
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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