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

HRID 1284933ノート

反応式

HRID 1284933 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-256b455fa34f45f58ceec2fc7c634445
出典データセット
uspto-grants-1986_01
特許番号
US04564638

反応ノート

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