Chloroacetone → HCID 22290993, compound

HRID 967703Notes

Reaction equation

HRID 967703 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:12])=[N:8][NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].Cl[CH2:16][C:17](=[O:19])[CH3:18]>CN(C=O)C.[Cl-].[NH4+]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:12])=[N:8][N:9]2[CH2:16][C:17](=[O:19])[CH3:18])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 178487565HCID 178487565, compound

Product 1

HCID 22290993HCID 22290993, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product from Step A (1.1 g, 6.7 mmol) in DMF (10 ml) was added sodium hydride (60% in oil, 0.41 g, 10.2 mmol) at room temperature. After stirring for 30 min, chloroacetone (0.79 ml, 10.2 mmol) was added, and the solution heated at 60° C. for 6 h. The reaction mixture was diluted with a saturated aqueous solution of ammonium chloride (10 ml) and extracted with ethyl acetate (3×65 ml). The combined extracts were washed with brine (10 ml), dried (MgSO4), and evaporated to give a residue which was purified by chromatography (silica, 20% to 30% ethyl acetate in hexane) to give an oil (1.3 g, 88%): MS (ES) m/z 219 (M+).

Workup

  1. extractionextracted with ethyl acetate (3×65 ml)
  2. washThe combined extracts were washed with brine (10 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a residue which
  6. customwas purified by chromatography (silica, 20% to 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8ed6c82238cd489388a9b8cf586300d9
Source dataset
uspto-grants-2005_10
Patent number
US06956036B1

Reaction notes

Loading…