N-bromobutanimide → HCID 23369697, compound

HRID 1900788Notes

Reaction equation

HRID 1900788 reaction equation
[CH2:1]([C:4]1[C:5]([OH:18])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[NH:10][C:9](=[O:15])[C:8]([CH3:16])=[C:7]2[CH3:17])[CH:2]=[CH2:3].[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:19][CH2:3][CH:2]1[O:18][C:5]2=[C:6]3[C:11](=[C:12]([CH3:14])[CH:13]=[C:4]2[CH2:1]1)[NH:10][C:9](=[O:15])[C:8]([CH3:16])=[C:7]3[CH3:17]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 23369617HCID 23369617, compound

Product 1

HCID 23369697HCID 23369697, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

6-Allyl-5-hydroxy-3,4,8-trimethylcarbostyril (1.01 g, 4.16 mmol) was dissolved in chloroform (50 ml). To the obtained solution, N-bromosuccinimide (888 mg, 4.99 mmol) was added. The mixture was refluxed with in a bath of 100° C. for 1.5 hours. The reaction mixture was cooled, washed with saturated aqueous NaCl solution and dried. The solvent was distilled off under reduced pressure. The residue was recrystallized from chloroform--ether to obtain 1.06 g of the title compound as yellow needles (79.8%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with saturated aqueous NaCl solution
  3. customdried
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-6c23c4c54e214467baaa962ca86f876e
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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