N-bromobutanimide → HCID 23369656, compound

HRID 1900839Notes

Reaction equation

HRID 1900839 reaction equation
[OH:1][C:2]1[C:11]([CH:12]([CH3:15])[CH:13]=[CH2:14])=[CH:10][C:9]([CH3:16])=[C:8]2[C:3]=1[CH2:4][C:5]([CH3:19])([CH3:18])[C:6](=[O:17])[NH:7]2.[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:20][CH2:14][CH:13]1[O:1][C:2]2=[C:3]3[C:8](=[C:9]([CH3:16])[CH:10]=[C:11]2[CH:12]1[CH3:15])[NH:7][C:6](=[O:17])[C:5]([CH3:18])([CH3:19])[CH2:4]3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 23369784HCID 23369784, compound

Product 1

HCID 23369656HCID 23369656, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 5-hydroxy-6-(1-methyl-2-propenyl)-3,3,8-trimethyl-3,4-dihydrocarbostyril (1.6 g, 6.2 mmol) and N-bromosuccinimide (1.2 g, 6.5 mmol) in chloroform (20 ml) was refluxed while stirring for 1 hour. Chloroform was added to the reaction mixture, followed by washing with water, and drying. The solvent was evaporated, and the residue was recrystallized from ethyl acetate-hexane. 1.9 g of the title compound was obtained as colorless crystals (90.6%).

Workup

  1. washby washing with water
  2. customdrying
  3. customThe solvent was evaporated
  4. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5823cc14e51545c4ae5bddf5775b6869
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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