N-bromobutanimide → HCID 86683660, compound

HRID 1509293Notes

Reaction equation

HRID 1509293 reaction equation
[Br:1][C:2]1[CH:12]=[N:11][C:5]2[O:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.C1C(=O)N([Br:20])C(=O)C1>CN(C=O)C.C(OCC)(=O)C.O>[Br:20][C:12]1[C:2]([Br:1])=[CH:3][C:4]2[NH:9][C:8](=[O:10])[CH2:7][O:6][C:5]=2[N:11]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 45901417-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazin-2-one

Product 1

HCID 86683660HCID 86683660, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (1.5 g, 6.55 mmol) and NBS (5.83, 32.7 mmol) were heated to 80° C. in DMF (30 ml) for 2 hours. The resulting reaction mixture was diluted with ethyl acetate (30 ml) and water (30 ml). The aqueous phase was extracted with fresh ethyl acetate (50 ml×3) and the combined organic layers were washed with brine (50 ml), dried on anhydrous Na2SO4, filtered and concentrated to dryness under reduced pressure to give the title compound (1.6 g, 79%). It was used for the next step without further purification. LCMS (Method D): RT=0.91 min, M+1=309.

Workup

  1. customThe resulting reaction mixture
  2. extractionThe aqueous phase was extracted with fresh ethyl acetate (50 ml×3)
  3. washthe combined organic layers were washed with brine (50 ml)
  4. dry with materialdried on anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-423e404bb1c24716832eb181cfcc10fd
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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