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

HRID 1284933노트

반응식

HRID 1284933 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-256b455fa34f45f58ceec2fc7c634445
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04564638

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