N-bromobutanimide → HCID 68539435, compound

HRID 1446696Notes

Reaction equation

HRID 1446696 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:12]N1C(=O)CCC1=O>C(#N)C.CCOC(C)=O>[Br:12][C:10]1[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][C:7]([NH2:11])=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 123519414-(tert-Butyl)pyridin-2-amine

Product 1

HCID 68539435HCID 68539435, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 4-tert-butyl-pyridin-2-ylamine (3 g, 20 mmol) in anhydrous acetonitrile (25 mL). Add N-bromosuccinimide (3.56 g, 20 mmol). Stir the reaction in the dark for overnight at room temperature. Dilute with EtOAc and wash with 1 N NaOH (aq.) and saturated aqueous sodium bicarbonate. Extract the organic layer. Wash the aqueous layer further with DCM. Dry the combined organic layers (MgSO4), and purify by silica gel column chromatography (EtOAc/hexane) to yield 2 g of the title compound (44%). LCMS (ES), m/z 231 (M+1).

Workup

  1. customthe reaction in the dark for overnight at room temperature
  2. washwash with 1 N NaOH (aq.) and saturated aqueous sodium bicarbonate
  3. extractionExtract the organic layer
  4. washWash the aqueous layer further with DCM
  5. dry with materialDry the combined organic layers (MgSO4)
  6. custompurify by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-5707850d380c457e9a21694d81a6acf6
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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