N-bromobutanimide → (3S)-3-[(4-bromophenyl)amino]butanenitrile

HRID 2041732Notes

Reaction equation

HRID 2041732 reaction equation
[C:1]1([NH:7][C@@H:8]([CH3:12])[CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:20])C(=O)C1>CN(C)C=O>[Br:20][C:4]1[CH:5]=[CH:6][C:1]([NH:7][C@@H:8]([CH3:12])[CH2:9][C:10]#[N:11])=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 39235654(3S)-3-(phenylamino)butanenitrile

Product 1

HCID 67173345(3S)-3-[(4-bromophenyl)amino]butanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3S)-3-(Phenylamino)butanenitrile (for a preparation see Intermediate 105) (11.3526 g, 70.9 mmol) was taken up in N,N-dimethylformamide (DMF) (200 mL) under nitrogen and cooled in an ice-bath. NBS (12.61 g, 70.9 mmol) was added and the reaction stirred. After 20 min, the reaction was partitioned between EtOAc (1000 mL) and water (500 mL). The organic layer was washed with 2M NaOH×2, water and brine (500 mL each) and then dried with Na2SO4, filtered and concentrated to yield the product as a cream solid (17.3 g).

Workup

  1. temperaturecooled in an ice-bath
  2. customthe reaction was partitioned between EtOAc (1000 mL) and water (500 mL)
  3. washThe organic layer was washed with 2M NaOH×2, water and brine (500 mL each)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-88c81fba31bf42388be2f855e92a9935
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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