Benzoyl Peroxide → HCID 86617377, compound

HRID 642561Notes

Reaction equation

HRID 642561 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[S:14][C:8]=2[C:7]=1[OH:19])=[O:5])[CH3:2].[Br:20]NC(=O)CCC(N)=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:20])[C:9]2[N:12]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[S:14][C:8]=2[C:7]=1[OH:19])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 9834204N-BromosuccinamideHCID 68426440HCID 68426440, compound

Product 1

HCID 86617377HCID 86617377, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2-tert-butyl-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (3.87 g, 13.8 mmol, example 166(d)), N-bromosuccinamide (2.67 g, 15 mmol), and benzoyl peroxide (315 mg, 1.3 mmol) in 46 mL of carbon tetrachloride was heated at reflux temperature for 4 h. The reaction mixture was concentrated under reduced pressure and purified by column chromatography, eluting the desired product from silica gel with a gradient of 0-30% ethyl acetate in hexanes to give 3.4 g of the title compound. MS (ESI−): 356.99, 358.98 e/z (M−1, 79Br/81Br).

Workup

  1. temperatureat reflux temperature for 4 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by column chromatography
  4. washeluting the desired product from silica gel with a gradient of 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2a2aac2bbaea45fc9f3fb17363a259cf
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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