N-bromobutanimide → HCID 136344015, compound

HRID 1847217Notes

Reaction equation

HRID 1847217 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][S:12][C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[C:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:13][S:12][C:9]2=[C:10]([Br:22])[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 136343974HCID 136343974, compound

Product 1

HCID 136344015HCID 136344015, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-hydroxy-3-phenyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (1.07 g, 3.56 mmol) in CCl4 was added N-bromosuccinimide (666 mg, 3.74 mmol) and benzoyl peroxide (43.1 mg, 0.18 mmol). The reaction mixture was refluxed with stirring for 4 h. After cooling to r. t. the mixture was filtered. The filtrate was concentrated in vacuo and purified by flash column chromatography on silica gel. Elution with 0-20% EtOAc/CH2Cl2, gave the title compound as white solid (1.08 g): MS (m/z) 378.9, 380.9 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. temperatureAfter cooling to r
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by flash column chromatography on silica gel
  6. washElution with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-d6cb43290f4d4a34a4cb445a078b83ec
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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