Aniline → N-Bicyclo[2.2.1]heptan-2-yl-N-[(4-chlorophenyl)methyl]-N'-phenylurea

HRID 1284933Notes

Reaction equation

HRID 1284933 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][N:14]([CH:18]2[CH2:23][CH:22]3[CH2:24][CH:19]2[CH2:20][CH2:21]3)[C:15](Cl)=[O:16])=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][N:14]([CH:18]2[CH2:23][CH:22]3[CH2:24][CH:19]2[CH2:20][CH2:21]3)[C:15]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 13564371Bicyclo[2.2.1]heptan-2-yl[(4-chlorophenyl)methyl]carbamyl chloride

Product 1

HCID 13564372N-Bicyclo[2.2.1]heptan-2-yl-N-[(4-chlorophenyl)methyl]-N'-phenylureaYield 64.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Aniline (19 g) was dissolved in 400 ml of toluene, and with stirring and cooling, a solution of 30 g of N-4-chlorobenzyl-N-2-norbornylcarbamoyl chloride in 50 ml of toluene was added dropwise. After the addition, the temperature of the mixture was gradually raised, and it was stirred for about 10 hours at about 70° to 80° C. After cooling, the precipitated aniline hydrochloride was separated by filtration. The toluene layer was washed successively with water, a 1% aqueous solution of sodium carbonate, 1% hydrochloric acid and then water, and then dried over anhydrous sodium sulfate. Toluene was evaporated, and the residue was recrystallized from a mixture of hexane and ethanol to give 23 g of the desired 1-(4-chlorobenzyl)-1-(2-norbornyl)-3-phenylurea. mp. 111°-113° C.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. temperaturethe temperature of the mixture was gradually raised
  4. stirringit was stirred for about 10 hours at about 70° to 80° C
  5. temperatureAfter cooling
  6. customthe precipitated aniline hydrochloride was separated by filtration
  7. washThe toluene layer was washed successively with water
  8. dry with materiala 1% aqueous solution of sodium carbonate, 1% hydrochloric acid and then water, and then dried over anhydrous sodium sulfate
  9. customToluene was evaporated
  10. customthe residue was recrystallized from a mixture of hexane and ethanol

Sources & evidence

ORD record
ord-256b455fa34f45f58ceec2fc7c634445
Source dataset
uspto-grants-1986_01
Patent number
US04564638

Reaction notes

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