Dimethylformamide → HCID 53832421, compound

HRID 2051742Notes

Reaction equation

HRID 2051742 reaction equation
O=P(Cl)(Cl)[Cl:3].CN([CH:9]=[O:10])C.[CH3:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18](OC)=[CH:17][CH:16]=1)=O.[C:23]([O-:26])(=O)C.[Na+]>C1(C)C=CC=CC=1>[Cl:3][C:13]([C:15]1[CH:16]=[CH:17][C:18]([O:10][CH3:9])=[CH:19][CH:20]=1)=[C:12]([CH3:11])[CH:23]=[O:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 671444-PropanoylanisoleHCID 517045Sodium Acetate

Product 1

HCID 53832421HCID 53832421, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

POCl3 (185 g) was added to 185 g of DMF at such a rate as to maintain the temperature below 25° by ice bath cooling. After stirring for 30 min, 4-methoxypropiophenone (82.1 g) was added dropwise to the mixture at 60°-65°. The reaction was maintained at 80°-90° for 8 hrs. Toluene (174 g) was added and 1-liter of a saturated sodium acetate solution was added so that a temperature of 65° was maintained by ice bath cooling. After heating at 70°-80° for 2 hrs. the organic phase was separated and washed with 300 ml of 5% NaHCO3. Distillation yielded 90 g (86%) of the desired product, bp 130° (1.0 mm).

Workup

  1. temperatureto maintain the temperature below 25° by ice bath
  2. temperaturecooling
  3. temperatureThe reaction was maintained at 80°-90° for 8 hrs
  4. temperaturewas maintained by ice bath
  5. temperaturecooling
  6. temperatureAfter heating at 70°-80° for 2 hrs
  7. customthe organic phase was separated
  8. washwashed with 300 ml of 5% NaHCO3
  9. distillationDistillation

Sources & evidence

ORD record
ord-02cbb29ab6284766b7a6907dfcf2de18
Source dataset
uspto-grants-1980_01
Patent number
US04182730

Reaction notes

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