Benzoyl Peroxide → HCID 68297625, compound

HRID 1410943Notes

Reaction equation

HRID 1410943 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([CH2:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[C:6]=1[CH3:19])=[O:4].[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([CH2:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[C:6]=1[CH2:19][Br:20])=[O:4]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68297702HCID 68297702, compound

Product 1

HCID 68297625HCID 68297625, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-bromo-2-methyl-6-oxo-1-thiazol-2-ylmethyl-1,6-dihydro-pyridine-3-carboxylic acid methyl ester (0.551 g, 1.61 mmol), N-bromosuccinimide (0.315 g, 1.77 mmol), and benzoyl peroxide (39 mg, 0.161 mmol) in CCl4 (20 mL) was refluxed for 16 h. The solvent was evaporated in vacuo, and the residue was chromatographed (0-60% EtOAc/hexanes) to give 100 mg of the title compound as a orange viscous oil. MS: (+) m/z 423.03 (M+1).

Workup

  1. temperaturewas refluxed for 16 h
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was chromatographed (0-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7f63ad08a27a407589e9b0ff07bd9df7
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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