Sodium Hydroxide → N-allyl-N-phenethylsorbamide

HRID 1654657

Reaction equation

HRID 1654657 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 20076663N-allyl-N-phenethylsorbamideYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 temperature 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.

Workup

  1. customthe temperature 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

Sources & evidence

ORD record
ord-a081a1e81730462ba3255f9bd73d41cd
Source dataset
uspto-grants-1995_04
Patent number
US05409929

Linked notes

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