Aniline → N-Butan-2-yl-N-[(4-chlorophenyl)methyl]-N'-phenylthiourea

HRID 259286Notes

Reaction equation

HRID 259286 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)=[S: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)=[S:16])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 21424194HCID 21424194, compound

Product 1

HCID 13018270N-Butan-2-yl-N-[(4-chlorophenyl)methyl]-N'-phenylthioureaYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

19 g of aniline were dissolved in 300 ml of toluene. To the resulting solution, a solution of 28 g of N-(4-chlorobenzyl)-N-sec.-butyl-thiocarbamoyl 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 then 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 cold 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 23 g of N-(4-chlorobenzyl)-N-sec.-butyl-N'-phenylthiourea were obtained. Yield: 70%. Melting point: 134°-134.5° C.

Workup

  1. temperatureunder cooling
  2. additionAfter the dropwise addition
  3. temperaturethe temperature of the solution was gradually raised
  4. stirringthe 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 cold 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-053fc547dd1b40248e66a9db50569a91
Source dataset
uspto-grants-1977_07
Patent number
US04036986

Reaction notes

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