2-Chloroethyl isocyanate → 1-(p-Acetamidophenyl)-3-(2-chloroethyl) urea

HRID 979885Notes

Reaction equation

HRID 979885 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[CH:4][CH:3]=1.[Cl:12][CH2:13][CH2:14][N:15]=[C:16]=[O:17]>CN(C)C=O>[C:7]([NH:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:16]([NH:15][CH2:14][CH2:13][Cl:12])=[O:17])=[CH:11][CH:10]=1)(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 312304-Aminoacetanilide

Product 1

HCID 2866861-(p-Acetamidophenyl)-3-(2-chloroethyl) urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1800 g of p-aminoacetanilide in 7000 ml of dimethylformamide is stirred at room temperature. The solution is then cooled to 10°-15° in an ice-water bath. To the stirred cooled solution is added 1440 g of 2-chloroethyl isocyanate in a thin stream over a 50-minute period, keeping the reaction mixture temperature between 20° and 25°. The reaction mixture is stirred at room temperature for 90 minutes; 8000 ml of ice-water is added over a 20-minute period. After stirring for an additional 2 hours, the solid is filtered off and washed with 4000 ml of water. The crude product is slurried with 7000 ml of 95% alcohol. The solid is filtered off and air-dried overnight at room temperature to give 1-(p-acetamidophenyl)-3-(2-chloroethyl)-urea, m.p. 207°-9° dec.

Workup

  1. temperatureThe solution is then cooled to 10°-15° in an ice-water bath
  2. temperatureTo the stirred cooled solution
  3. customthe reaction mixture temperature between 20° and 25°
  4. stirringAfter stirring for an additional 2 hours
  5. filtrationthe solid is filtered off
  6. washwashed with 4000 ml of water
  7. filtrationThe solid is filtered off
  8. customair-dried overnight at room temperature

Sources & evidence

ORD record
ord-d8d664a76eb7478e84757d4e171473ec
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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