Dimethylformamide → HCID 54099408, compound

HRID 2216728Notes

Reaction equation

HRID 2216728 reaction equation
O=P(Cl)(Cl)[Cl:3].CN([CH:9]=[O:10])C.[C:11]1([C:17]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(=O)C.[Na+]>O>[Cl:3][C:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[C:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 99482-PhenylacetophenoneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

Product 1

HCID 54099408HCID 54099408, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.25 mol (23 mL) of POCl3 was added at 0° C. to a 0.3 mol (23.5 mL) of DMF. 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 0.1 mol (19.6 g) of deoxybenzoin. The resulting reaction mixture was allowed to reach room temperature, stirred for 12 h at the same temperature and subsequently heated at 100° C. for 2 h. Finally it was poured into a mixture of ice and 10% solution of sodium acetate in water. The oily precipitate was filtered and washed with cold methanol and hexane. The residue was crystallized. Yield 18.5 g (76%).

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 for 12 h at the same temperature
  6. temperaturesubsequently heated at 100° C. for 2 h
  7. filtrationThe oily precipitate was filtered
  8. washwashed with cold methanol and hexane
  9. customThe residue was crystallized

Sources & evidence

ORD record
ord-3b4acb3725cd4235a448593056285855
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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