Dimethylformamide → HCID 178433892, compound

HRID 555608Notes

Reaction equation

HRID 555608 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([OH:16])=[CH:14][C:13]([CH3:17])=[N:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)=O.CN(C)[CH:25]=[O:26]>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([OH:16])=[C:14]([CH:25]=[O:26])[C:13]([CH3:17])=[N:12]2)=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178429256HCID 178429256, compound

Product 1

HCID 178433892HCID 178433892, compoundYield 70%

Conditions

Temperature
100 °C

Procedure

1.89 g (9.33 mmol) of 1-(4-tert-butylphenyl)-5-hydroxy-3-methyl-1H-pyrazole was dissolved in 3.6 ml of dry dimethylformamide, and 1.05 ml (11.26 mmol) phosphorus oxychloride was added gradually at 20° C. or below under cooling with ice. After the addition, the mixture was heated at 100° C. for 3 hours, then cooled to room temperature and poured into 30 ml of ice-cold water. The mixed solution was stirred at room temperature for 18 hours, and the precipitated solid was collected by filtration, washed with 20 ml of water and dried to obtain 1.61 g of the above-identified desired product as a yellow solid (yield 70%).

Workup

  1. temperatureunder cooling with ice
  2. additionAfter the addition
  3. temperaturecooled to room temperature
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with 20 ml of water
  6. customdried

Sources & evidence

ORD record
ord-9788b77102954d5598b2c9497e32e4fa
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Reaction notes

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