N-bromobutanimide → 2-Acetylamino-5-bromo-3-cyanothiophene

HRID 900445

Reaction equation

HRID 900445 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:10]#[N:11])(=[O:3])[CH3:2].[Br:12]N1C(=O)CCC1=O>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([Br:12])=[CH:8][C:9]=1[C:10]#[N:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 676450N-(3-cyanothiophen-2-yl)acetamide

Product 1

HCID 130528502-Acetylamino-5-bromo-3-cyanothiophene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Acetylamino-3-cyanothiophene (13.5 g) was dissolved in dimethylformamide (110 ml) and cooled in an ice/water bath. N-Bromosuccinimide (15.9 g) was added portion wise over 20 minutes and then the mixture warmed to room temperature and stirred for 3 h. The mixture was concentrated to approximately half the volume and water added to precipitate the product. This was filtered off and dried at 60° C. under vacuum (18.8 g).

Workup

  1. temperaturecooled in an ice/water bath
  2. concentrationThe mixture was concentrated to approximately half the volume and water
  3. additionadded
  4. customto precipitate the product
  5. filtrationThis was filtered off
  6. customdried at 60° C. under vacuum (18.8 g)

Sources & evidence

ORD record
ord-f0baf2de5c144b1dbe1e459fa3ce055a
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Linked notes

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