N,N-Dimethylaniline → N-Benzyl-N-butyl-N'-(3-chlorophenyl)-N'-phenylurea

HRID 2418688Notes

Reaction equation

HRID 2418688 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](Cl)(Cl)=[O:16].CN(C)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[CH2:8]([N:7]([CH2:1][CH2:2][CH2:3][CH3:4])[C:15]([N:7]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:16])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 6371PhosgeneHCID 75453-Chlorodiphenylamine

Product 1

HCID 13339984N-Benzyl-N-butyl-N'-(3-chlorophenyl)-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 5.09 g. of N-phenyl-3-chloraniline in 20 ml. of toluene is added to a solution of 4.70 g. of phosgene and 3.64 g. of N,N-dimethylaniline in 55 ml. of toluene and the mixture is warmed to 400° C. and then stirred while cooling to room temperature during 45 minutes. The mixture is extracted with water and the organic layer is separateld and evaporated to about one-half its volume. To this solution is added 100 ml. of toluene followed by 9.80 g. of N-benzyl-n-butylamine. The resulting mixture is sitrred under reflux for 30 minutes and then washed with water, 1N hydrochloric acid, and saturated sodium bicarbonate solution. The organic layer is separated, dried over sodium sulfate, decolorized using activated charcoal, and evaporated. The residue is evaporatively distilled at 185°-190° C. under reduced pressure (105 microns) to yield 1-benzyl-1-(n-butyl)-3-(3-chlorophenyl)-3-phenylurea as a viscous, pale-yellow liquid.

Workup

  1. extractionThe mixture is extracted with water
  2. customevaporated to about one-half its volume
  3. additionTo this solution is added 100 ml
  4. temperatureunder reflux for 30 minutes
  5. washwashed with water, 1N hydrochloric acid, and saturated sodium bicarbonate solution
  6. customThe organic layer is separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. distillationThe residue is evaporatively distilled at 185°-190° C. under reduced pressure (105 microns)

Sources & evidence

ORD record
ord-14035cac973146b08c3c151c9a4736b1
Source dataset
uspto-grants-1984_09
Patent number
US04473579

Reaction notes

Loading…