N-bromobutanimide → HCID 19018248, compound

HRID 1728448Notes

Reaction equation

HRID 1728448 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH:7]2[C:13](=[O:14])[NH:12][C:10](=[O:11])[CH:9]([C:15]([OH:17])=[O:16])[CH2:8]2)=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:20][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[C:13](=[O:14])[NH:12][C:10](=[O:11])[CH:9]([C:15]([OH:17])=[O:16])[CH2:8]2)=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 19018238HCID 19018238, compound

Product 1

HCID 19018248HCID 19018248, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 1.3 g (5.2 mmol) of 4-(4-methylphenoxy)carboxyglutarimide, 1.0 g (5.7 mmol) of N-bromosuccinimide and 0.02 g of benzoyl peroxide in 30 ml of carbon tetrachloride was refluxed for 16 hours, cooled to room temperature, evaporated and the residue dissolved in 200 ml of ethyl acetate. The EtOAc layer was washed with water, dried over Na2SO4 and evaporated to give 1.6 g of the crude product.

Workup

  1. customevaporated
  2. dissolutionthe residue dissolved in 200 ml of ethyl acetate
  3. washThe EtOAc layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-a3f70a8de1034717b4fb9f7aecd76d6a
Source dataset
uspto-grants-1994_07
Patent number
US05326905

Reaction notes

Loading…