Benzoyl Peroxide → HCID 18700307, compound

HRID 1604288Notes

Reaction equation

HRID 1604288 reaction equation
[C:1]([NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([O:14][CH3:15])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][Br:17])=[C:9]([O:14][CH3:15])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 18700304HCID 18700304, compound

Product 1

HCID 18700307HCID 18700307, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 3 g of N-tert-butyl-4-methyl-3-methoxybenzamide, 2.4 g of N-bromosuccinimide and 0.16 g of benzoyl peroxide in 40 ml of carbon tetrachloride is stirred at 30° C. while irradiating in the visible spectrum for 48 hours. The solvent is evaporated and then, successively, 25 ml of water are added, extraction is carried out with diethyl ether, drying is carried out over MgSO4, the solvent is evaporated and the residue is chromatographed on silica gel, elution being carried out with an 8/2 (v/v) cyclohexane/ethyl acetate mixture. The expected reactant is isolated after crystallization from isopropyl ether; M.p.=114° C.

Workup

  1. customwhile irradiating in the visible spectrum for 48 hours
  2. customThe solvent is evaporated
  3. additionsuccessively, 25 ml of water are added
  4. extractionextraction
  5. customdrying
  6. customthe solvent is evaporated
  7. customthe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-bbf8dacc7e4849639975ca9d8bda5240
Source dataset
uspto-grants-1999_11
Patent number
US05994350

Reaction notes

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