Bromoacetonitrile → HCID 22449545, compound

HRID 2257852Notes

Reaction equation

HRID 2257852 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]2[C:6]=1[C:7](=[O:16])[CH2:8][CH2:9][NH:10]2)(=[O:3])[CH3:2].Br[CH2:18][C:19]#[N:20]>CN(C=O)C>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]2[C:6]=1[C:7](=[O:16])[CH2:8][CH2:9][N:10]2[CH2:18][C:19]#[N:20])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11534BromoacetonitrileHCID 22449436HCID 22449436, compound

Product 1

HCID 22449545HCID 22449545, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound prepared in (1) above (1.95 gm) was dissolved into 40 ml of DMF, and 6 ml of bromoacetonitrile was added to the solution. After heating under reflux for 3 hours, the reaction mixture was concentrated, and chloroform was added to the residue. The residue, after washing with saturated brine, was dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was subjected to silica gel column chromatography using a chloroform-methanol (100:1) mixed solvent as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 605 mg of the title compound.

Workup

  1. additionwas added to the solution
  2. temperatureAfter heating
  3. temperatureunder reflux for 3 hours
  4. concentrationthe reaction mixture was concentrated
  5. additionchloroform was added to the residue
  6. washThe residue, after washing with saturated brine
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customAfter evaporating the solvent
  9. additionmixed solvent as an eluant
  10. customto obtain fractions
  11. additioncontaining the target compound
  12. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-dccd286414de4786980f5b582186b68c
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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