1H-Pyrazol-5-ol, 3-methyl-1-phenyl- → HCID 18457995, compound

HRID 1363906Notes

Reaction equation

HRID 1363906 reaction equation
[CH3:1][C:2]1[NH:3][N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5](=[O:7])[CH:6]=1.[OH-].[Ca+2].[OH-].[C:17](CC(Cl)=O)([CH3:20])([CH3:19])[CH3:18]>Cl>[C:17]([C:6]1[C:5](=[O:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:3][C:2]=1[CH3:1])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 703351H-Pyrazol-5-ol, 3-methyl-1-phenyl-HCID 815143,3-Dimethylbutanoyl chlorideHCID 6093208Calcium Hydroxide

Product 1

HCID 18457995HCID 18457995, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-Methyl-1-phenylpyrazol-5-one (5 g; 0.029 mole) was placed in a flask equipped with a stirrer and reflux condenser. Dry and distilled dioxane (40 ml) was added by warming and to the clear solution calcium hydroxide (6.4 g; 0.086 mole) was added followed by drop wise addition of tert-butylacetyl chloride (4.8 ml; 0.034 mole). The mixture was heated to reflux for 4 hours and then poured into 2M HCl (200 ml) to decompose the calcium complex. A light brown precipitate formed immediately, which was filtered off under suction after refrigerating overnight. The product washed with water and dried under vacuum at 50° C. The product was recrystallised from methanol to give an off-white crystalline solid, m.p 85-86° C.; 6.8 g (82%).

Workup

  1. customequipped with a stirrer
  2. temperaturereflux condenser
  3. customDry
  4. distillationdistilled dioxane (40 ml)
  5. additionwas added
  6. additionwas added
  7. temperatureThe mixture was heated
  8. temperatureto reflux for 4 hours
  9. customA light brown precipitate formed immediately
  10. filtrationwhich was filtered off under suction
  11. washThe product washed with water
  12. customdried under vacuum at 50° C
  13. customThe product was recrystallised from methanol
  14. customto give an off-white crystalline solid, m.p 85-86° C.

Sources & evidence

ORD record
ord-80c1c03b410841578ffd5e82f18e9e75
Source dataset
uspto-grants-2011_02
Patent number
US07887933B2

Reaction notes

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