Sodium Hydroxide → N-allyl-N-phenethylsorbamide

HRID 1586774

反応式

HRID 1586774 の反応式
[C:1](Cl)(=[O:7])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6].[CH2:9]([NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:10]=[CH2:11].[OH-].[Na+]>C(Cl)Cl>[CH2:9]([N:12]([CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:1](=[O:7])/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6])[CH:10]=[CH2:11]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 5368941(2E,4E)-hexa-2,4-dienoyl chlorideHCID 10012381(2-phenylethyl)(prop-2-en-1-yl)amine

生成物 1

HCID 20076663N-allyl-N-phenethylsorbamide収率 100.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Sorboyl chloride (3.53 g) was added to a mixture of 4.0 g of N-allylphenethylamine, 25 mL of methylene chloride and 25 mL of 15% aqueous sodium hydroxide, keeping the temperatue below 15°. The mixture was stirred in an ice bath for 1 hour, then at room temperature overnight. The aqueous layer was extracted several times with toluene and the combined organic phases were washed successively with 5% hydrochloric acid, water, and 10% sodium carbonate solution. Removal of the solvents gave 6.37 g of N-allyl-N-phenethylsorbamide. This product was heated under reflux in 50 mL of p-xylene for 10 hours. Removal of the solvent gave 6-methyl-3a,4,5,7a-tetrahydroisoindolin-1-one as a mixture of isomers still containing about 10% of the uncyclized starting material.

後処理

  1. customthe temperatue below 15°
  2. customat room temperature
  3. customovernight
  4. extractionThe aqueous layer was extracted several times with toluene
  5. washthe combined organic phases were washed successively with 5% hydrochloric acid, water, and 10% sodium carbonate solution
  6. customRemoval of the solvents

出典と根拠

ORDレコード
ord-fc33e192ad0448cbbd085bb060d65173
出典データセット
uspto-grants-1993_06
特許番号
US05216018

関連ノート

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