Benzoyl Peroxide → HCID 86617358, compound

HRID 642370Notes

Reaction equation

HRID 642370 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[S:14][C:8]=2[C:7]=1[OH:23])=[O:5])[CH3:2].[Br:24]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([Br:24])[C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[S:14][C:8]=2[C:7]=1[OH:23])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68428390HCID 68428390, compound

Product 1

HCID 86617358HCID 86617358, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 7-hydroxy-2-(3-methoxy-phenyl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (643 mg, 1.95 mmole), N-bromosuccinimide (364 mg, 2.04 mmole) and benzoyl peroxide (23 mg, 9.74 mmole) in carbon tetrachloride (9.5 ml) was refluxed for 5 h before it was cooled to room temperature and partitioned between dichloromethane and water. The organic layer was washed with saturated aqueous sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a white solid (338 mg). MS: (+) m/z 409.11, 411.11 (M+1, 79Br/81Br).

Workup

  1. temperaturewas refluxed for 5 h before it
  2. custompartitioned between dichloromethane and water
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-a5acf015acb64066aaf42dd9014fdfb9
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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