Dimethylformamide → HCID 45790876, compound

HRID 2216724Notes

Reaction equation

HRID 2216724 reaction equation
O=P(Cl)(Cl)[Cl:3].CN([CH:9]=[O:10])C.[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=O)[CH2:12][CH3:13].C([O-])(=O)C.[Na+]>O>[Cl:3][C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[C:12]([CH3:13])[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 71481-Phenyl-1-propanoneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

Product 1

HCID 45790876HCID 45790876, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.2 mol (110 mL) of POCl3 was added at 0° C. to a 2.8 mol (216 mL) of DMF (excess of DMF used as solvent). At the end of the addition, the mixture was allowed to warm to room temperature and stirred for 1 h. Then it was cooled again to 0° C. and treated with 1 mol (134 g) of propiophenone. The resulting reaction mixture was allowed to reach room temperature and stirred overnight. Then it was poured into a mixture of ice and water, added of sodium acetate and extracted with CHCl3 (3×150 mL). The organic phase was separated, washed with water until neutral pH, dried over MgSO4 and evaporated off to dryness. The residue was distilled in vacuo, b.p. 120° C./10 torr. Yield 163 g (90%).

Workup

  1. additionAt the end of the addition
  2. temperatureThen it was cooled again to 0° C.
  3. customThe resulting reaction mixture
  4. customto reach room temperature
  5. stirringstirred overnight
  6. extractionextracted with CHCl3 (3×150 mL)
  7. customThe organic phase was separated
  8. washwashed with water until neutral pH
  9. dry with materialdried over MgSO4
  10. customevaporated off to dryness
  11. distillationThe residue was distilled in vacuo, b.p. 120° C./10 torr

Sources & evidence

ORD record
ord-7c6f82eee99243848ef464cb975773b3
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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