Toluene → N-n-Hexyl-aminocarbonyl-2-methylindoline

HRID 358330

反応式

HRID 358330 の反応式
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C([N:13]([CH2:16]C)CC)C.[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.ClC(OC1C=CC=CC=1)=[O:27]>O>[CH2:18]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][C:2]1([C:16]([NH2:13])=[O:27])[CH3:1])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

参加物

6

反応物 4

HCID 1140TolueneHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 233052-Methylindoline

生成物 1

HCID 70456382N-n-Hexyl-aminocarbonyl-2-methylindoline収率 53%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
20 °C

実験手順

A solution of 0.1 mole of 2-methylindoline, 0.12 mole of triethylamine, 100 ml of toluene and 0.1 mole of phenyl chloroformate is kept at 40° C. for 10 hours and is then cooled to 20° C. and stirred with 250 ml of water for 15 minutes. The toluene phase is separated off, the solvent is evaporated in vacuo, the residue is dissolved in 100 ml of n-hexylamine and this solution is heated under reflux at 130° C. for 6 hours. After cooling, the solvent is evaporated off at 50° C./10 mm Hg and the residue is taken up in 250 ml of toluene. The solution is then extracted successively with 200 ml of 1N sodium hydroxide solution, 200 ml of 1N hydrochloric acid and 200 ml of water. After concentrating the solution, the residue is recrystallised from petroleum ether. N-n-Hexyl-aminocarbonyl-2-methylindoline with a melting point of 57°-59° C. is obtained. Yield: 53% of theory.

後処理

  1. customThe toluene phase is separated off
  2. customthe solvent is evaporated in vacuo
  3. dissolutionthe residue is dissolved in 100 ml of n-hexylamine
  4. temperaturethis solution is heated
  5. temperatureunder reflux at 130° C. for 6 hours
  6. temperatureAfter cooling
  7. customthe solvent is evaporated off at 50° C./10 mm Hg
  8. extractionThe solution is then extracted successively with 200 ml of 1N sodium hydroxide solution, 200 ml of 1N hydrochloric acid and 200 ml of water
  9. concentrationAfter concentrating the solution
  10. customthe residue is recrystallised from petroleum ether

出典と根拠

ORDレコード
ord-8fd19334bfca46eb9aed2e5cc89d7b86
出典データセット
uspto-grants-1984_08
特許番号
US04466964

関連ノート

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