Benzoyl Peroxide → HCID 14153223, compound

HRID 648856Notes

Reaction equation

HRID 648856 reaction equation
[CH3:1][C:2]1[C:11]([S:12]([N:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.CCOCC>[Br:18][CH2:1][C:2]1[C:11]([S:12]([N:15]([CH3:17])[CH3:16])(=[O:13])=[O:14])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 13937642Methyl 3-[(dimethylamino)sulfonyl]-2-methylbenzoate

Product 1

HCID 14153223HCID 14153223, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 25.7 g of the product from Example 10, 17.8 g of N-bromosuccinimide, and 1.0 g benzoyl peroxide in 350 ml carbon tetrachloride was stirred at reflux temperature for 3.5 hours and then at room temperature overnight. The by-product succinimide was removed by filtration and the filtrate concentrated in vacuo to afford an oil which was dissolved in ether and washed with two portions of water. Drying and evaporation of the ether layer afforded a viscous yellow oil which was shown by 1H NMR analysis to consist of the title compound and unreacted starting material in a ratio of approximately 2:1. This mixture was carried directly on to the next step.

Workup

  1. temperatureat reflux temperature for 3.5 hours
  2. customat room temperature
  3. customovernight
  4. customThe by-product succinimide was removed by filtration
  5. concentrationthe filtrate concentrated in vacuo
  6. customto afford an oil which
  7. washwashed with two portions of water
  8. customDrying
  9. customevaporation of the ether layer
  10. customafforded a viscous yellow oil which

Sources & evidence

ORD record
ord-5baf883a48694dc7a2b98e617f92323f
Source dataset
uspto-grants-1988_04
Patent number
US04737185

Reaction notes

Loading…