N-bromobutanimide → HCID 68679677, compound

HRID 1725459Notes

Reaction equation

HRID 1725459 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[CH:8]=[CH:7][S:6][C:5]1=[N:9][C:10]1[N:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][CH:11]=1.[Br:20]N1C(=O)CCC1=O>O1CCOCC1.C(OCC)(=O)C>[Br:20][C:7]1[S:6][C:5](=[N:9][C:10]2[N:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:12][CH:11]=2)[N:4]([CH2:3][O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 68679074HCID 68679074, compound

Product 1

HCID 68679677HCID 68679677, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

6.38 g (20.6 mmol) of methyl 6-(3-methoxymethyl-3H-thiazol-2-ylideneamino)-pyridine-2-carboxylate was dissolved in 60 ml of 1,4-dioxane and 3.67 g (20.6 mmol) of N-bromosuccinimide was added thereto at room temperature. The reaction mixture was heated under reflux for 30 minutes, cooled to room temperature, diluted with 200 ml of ethyl acetate and washed with 150 ml of water for three times. After that, the reaction mixture was washed with 150 ml of brine, dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo to give 7.10 g (19.8 mmol) of the title compound as a white solid.

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. washwashed with 150 ml of water for three times
  5. washAfter that, the reaction mixture was washed with 150 ml of brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-14c518a9e3f244feb616de2c6111d129
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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