N-bromobutanimide → HCID 23369577, compound

HRID 1900850Notes

Reaction equation

HRID 1900850 reaction equation
[CH2:1]([C:4]1[C:5]([OH:19])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[NH:10][C:9](=[O:15])[C:8]([CH:16]([CH3:18])[CH3:17])=[CH:7]2)[CH:2]=[CH2:3].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:20][CH2:3][C:2]1[O:19][C:5]2=[C:6]3[C:11](=[C:12]([CH3:14])[CH:13]=[C:4]2[CH:1]=1)[NH:10][C:9](=[O:15])[C:8]([CH:16]([CH3:17])[CH3:18])=[CH:7]3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 23369633HCID 23369633, compound

Product 1

HCID 23369577HCID 23369577, compoundYield 109.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
75 °C

Procedure

6-Allyl-5-hydroxy-3-isopropyl-8-methylcarbostyril (1.50 g, 5.34 mmol) was dissolved in chloroform (100 ml). N-bromosuccinimide (1.10 g, 6.18 mmol) was added to the solution, and the mixture was stirred at 75° C. for 90 minutes. The reaction mixture was extracted from chloroform-water, and the organic phase was washed with saturated aqueous NaCl solution, dried, and condensed under reduced pressure. The residue was recrystallized from chloroform -ethyl acetate-ether to obtain 1.95 g of the title compound as pale yellow needles (99.4%).

Workup

  1. extractionThe reaction mixture was extracted from chloroform-water
  2. washthe organic phase was washed with saturated aqueous NaCl solution
  3. customdried
  4. customcondensed under reduced pressure
  5. customThe residue was recrystallized from chloroform -ethyl acetate-ether

Sources & evidence

ORD record
ord-8a5c030a2db941d7bff2193f4fbb570a
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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