N-bromobutanimide → HCID 136388303, compound

HRID 1034949Notes

Reaction equation

HRID 1034949 reaction equation
[CH3:1][C:2]1[C:14]2[C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=3[C:7](=[O:15])[NH:6][C:5]=2[N:4]([CH3:16])[N:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.CN(C=O)C.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:17][CH:12]1[CH2:11][CH2:10][CH2:9][C:8]2[C:7](=[O:15])[NH:6][C:5]3[N:4]([CH3:16])[N:3]=[C:2]([CH3:1])[C:14]=3[C:13]1=2

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 135512456HCID 135512456, compound

Product 1

HCID 136388303HCID 136388303, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of EXAMPLE 1 (966 mg, 4.45 mmol) in a mixture of chloroform (30 mL) and N,N′-dimethylformamide (2 mL) was treated with N-bromosuccinimide (791 mg, 4.45 mmol) and catalytic 2,2′-azobis(2-methylpropionitrile) (5 mg) at 65° C. for 18 hours. The mixture was cooled, concentrated and the residue partitioned between ethyl acetate and brine. The organic phase was washed with water, concentrated and purified by flash chromatography on silica gel eluting with 50% ethyl acetate in hexanes to provide 1.14 g (87%) of the title compound. MS (DCI/NH3) m/z 297 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customthe residue partitioned between ethyl acetate and brine
  4. washThe organic phase was washed with water
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel eluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2e672b73cab34b14b407e1651abee9e4
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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