Ethyl isocyanate → N-Bicyclo[2.2.1]heptan-2-yl-N-[(4-chlorophenyl)methyl]-N'-ethylurea

HRID 1284932Notes

Reaction equation

HRID 1284932 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][CH:8]2[CH2:13][CH:12]3[CH2:14][CH:9]2[CH2:10][CH2:11]3)=[CH:4][CH:3]=1.[CH2:17]([N:19]=[C:20]=[O:21])[CH3:18]>CCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH:8]2[CH2:13][CH:12]3[CH2:14][CH:9]2[CH2:10][CH2:11]3)[C:20]([NH:19][CH2:17][CH3:18])=[O:21])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 13255093HCID 13255093, compound

Product 1

HCID 13255094N-Bicyclo[2.2.1]heptan-2-yl-N-[(4-chlorophenyl)methyl]-N'-ethylureaYield 85.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

24 g of N-4-chlorobenzyl-2-norbornylamine was dissolved in 400 ml of hexane, and with stirring and cooling, a solution of 8 g of ethyl isocyanate in 30 ml of hexane was added dropwise to the solution. After the addition, the temperature of the mixture was gradually raised, and it was stirred for about 3 hours at 40° C. After cooling, the precipitated crystals were suction-filtered, and recrystallized from a mixture of hexane and ethanol to give 26.7 g of the desired 1-(4-chlorobenzyl)-3-ethyl-1-(2-norbornyl)urea. mp. 132°-133° C.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. temperaturethe temperature of the mixture was gradually raised
  4. stirringit was stirred for about 3 hours at 40° C
  5. temperatureAfter cooling
  6. filtrationthe precipitated crystals were suction-filtered
  7. customrecrystallized from a mixture of hexane and ethanol

Sources & evidence

ORD record
ord-2264b606c0634264a757ed863a28d451
Source dataset
uspto-grants-1986_01
Patent number
US04564638

Reaction notes

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