Propionyl chloride → N-(5-tert-Butyl-1H-pyrazol-3-yl)propanamide

HRID 2164497Notes

Reaction equation

HRID 2164497 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH:4][N:3]=1.[C:11](Cl)(=[O:14])[CH2:12][CH3:13]>O1CCOCC1>[C:7]([C:5]1[NH:4][N:3]=[C:2]([NH:1][C:11](=[O:14])[CH2:12][CH3:13])[CH:6]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 5227873-Amino-5-tert-butylpyrazole

Product 1

HCID 13235938N-(5-tert-Butyl-1H-pyrazol-3-yl)propanamideYield 80.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

20 g (0.14 mole) of 3-amino-5-t-butylpyrazole prepared in Example 1 was dissolved in 100 ml of dioxane, and 14 g of propionyl chloride was added thereto. The mixture was allowed to react at 80° C. for 5 hours. After completion of the reaction, the dioxane was distilled off under reduced pressure, and then water was added to the residue whereby the reaction product was dissolved therein. The resulting solution was neutralized with a 10% sodium hydroxide aqueous solution whereby crystals were precipitated. The crystals were collected by filtration, washed with water and benzene, and then dried to obtain 22 g of 5-t-butyl-3-propionylaminopyrazole. This product was recrystallized from methanol and found to have a melting point of 228° to 229° C.

Workup

  1. customto react at 80° C. for 5 hours
  2. customAfter completion of the reaction
  3. distillationthe dioxane was distilled off under reduced pressure
  4. additionwater was added to the residue whereby the reaction product
  5. dissolutionwas dissolved
  6. customwere precipitated
  7. filtrationThe crystals were collected by filtration
  8. washwashed with water and benzene
  9. customdried

Sources & evidence

ORD record
ord-625bedac77d54771a26c921fa2c0ee66
Source dataset
uspto-grants-1985_03
Patent number
US04505739

Reaction notes

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