Aniline → HCID 13018269, compound

HRID 596308Notes

Reaction equation

HRID 596308 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][N:14]([CH:18]([CH2:20][CH3:21])[CH3:19])[C:15](Cl)=[O:16])=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]([CH:18]([CH2:20][CH3:21])[CH3:19])[C:15]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:16])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 21452004N-[4-chlorobenzyl]-N-sec.-butyl-carbamoyl chloride

Product 1

HCID 13018269HCID 13018269, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

19 g (0.2 mole) of aniline were dissolved in 300 ml of toluene. To the resulting solution, a solution of 26 g (0.1 mole) of N-[4-chlorobenzyl]-N-sec.-butyl-carbamoyl chloride in 70 ml of toluene was added dropwise, under cooling and stirring. After the dropwise addition, the temperature of the solution was gradually raised, and the the solution was stirred at a temperature of 70°-80° C for about 5 hours. The solution was cooled to precipitate aniline hydrochloride, which was then separated by filtration. The toluene layer was washed with 100 ml of water and dried with anhydrous sodium sulfate. Then, the toluene was distilled off. The residue was subjected to recrystallization from a mixture of hexane and ethyl alcohol, whereby 26.3 g of N-(4-chlorobenzyl)-N-sec.-butyl-N'-phenylurea were obtained. Yield: 83%. Melting point: 80°-81.5° C.

Workup

  1. temperatureunder cooling
  2. additionAfter the dropwise addition
  3. temperaturethe temperature of the solution was gradually raised
  4. stirringthe the solution was stirred at a temperature of 70°-80° C for about 5 hours
  5. temperatureThe solution was cooled
  6. customto precipitate aniline hydrochloride, which
  7. customwas then separated by filtration
  8. washThe toluene layer was washed with 100 ml of water
  9. dry with materialdried with anhydrous sodium sulfate
  10. distillationThen, the toluene was distilled off
  11. customThe residue was subjected to recrystallization from a mixture of hexane and ethyl alcohol

Sources & evidence

ORD record
ord-8b0fd0eb184d4499a0e9b192cc33ca95
Source dataset
uspto-grants-1977_03
Patent number
US04010281

Reaction notes

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