Benzoyl Peroxide → HCID 18700307, compound

HRID 2288689Notes

Reaction equation

HRID 2288689 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, 0.16 g of benzoyl peroxide in 40 ml of carbon tetrachloride is stirred at 30° C., under irradiation with visible light for 48 hours. The solvent is evaporated off, then in succession 25 ml of water is added, the mixture is extracted with diethyl ether, dried over magnesium sulfate, the solvent is evaporated off and the residue is chromatographed on silica gel, eluting with an 8/2 cyclohexane/ethyl acetate (v/v) mixture. The expected reactant is isolated after crystallisation from isopropyl ether; M.p.=114° C.

Workup

  1. customThe solvent is evaporated off
  2. additionin succession 25 ml of water is added
  3. extractionthe mixture is extracted with diethyl ether
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent is evaporated off
  6. customthe residue is chromatographed on silica gel
  7. washeluting with an 8/2 cyclohexane/ethyl acetate (v/v) mixture

Sources & evidence

ORD record
ord-76c4ef8630fe4fe6b2ade9ef4266b27f
Source dataset
uspto-grants-2000_07
Patent number
US06090818

Reaction notes

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