Dimethylformamide → HCID 178426271, compound

HRID 555603Notes

Reaction equation

HRID 555603 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[NH:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].P(Cl)(Cl)(Cl)=O.CN(C)[CH:23]=[O:24]>>[CH3:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([OH:14])=[C:12]([CH:23]=[O:24])[C:11]([CH3:15])=[N:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 117358291-(3,4-Dimethylphenyl)-3-methyl-3-pyrazolin-5-one

Product 1

HCID 178426271HCID 178426271, compoundYield 49%

Conditions

Temperature
100 °C

Procedure

1.86 g (9.16 mmol) of 1-(3,4-dimethylphenyl)-3-methyl-3-pyrazolin-5-one was dissolved in 3.6 ml of dry dimethylformamide, and 1.02 ml (11.0 mmol) of phosphorus oxychloride was added gradually under cooling with ice at 20° C. or below. After the addition, the mixture was heated at 100° C. for 2 hours, cooled to room temperature and poured into 30 ml of ice-cold water. Then, the mixture was washed with 10 ml of water and 10 ml of dimethylformamide. The mixed solution was stirred for 18 hours, and the precipitated solid was collected by filtration, washed with 20 ml of water and dried to obtain 1.03 g of the desired product as a pale brown solid (yield 49%).

Workup

  1. temperatureunder cooling with ice at 20° C. or below
  2. additionAfter the addition
  3. temperaturecooled to room temperature
  4. washThen, the mixture was washed with 10 ml of water and 10 ml of dimethylformamide
  5. filtrationthe precipitated solid was collected by filtration
  6. washwashed with 20 ml of water
  7. customdried

Sources & evidence

ORD record
ord-60c9eece1ba045199c92a071372a279b
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Reaction notes

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