Benzoyl chloride → Benzamide, N-(5-methyl-1H-pyrazol-3-yl)-

HRID 1953803Notes

Reaction equation

HRID 1953803 reaction equation
C(=O)([O-])[O-].[Ca+2].[NH2:6][C:7]1[CH:11]=[C:10]([CH3:12])[NH:9][N:8]=1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCOCC1>[C:13]([NH:6][C:7]1[CH:11]=[C:10]([CH3:12])[NH:9][N:8]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 10112Calcium CarbonateHCID 931461H-Pyrazol-3-amine, 5-methyl-

Product 1

HCID 4247366Benzamide, N-(5-methyl-1H-pyrazol-3-yl)-Yield 24.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

103 g (1 mol) of calcium carbonate were added with stirring to a solution of 50 g (0.5 mol) of 3-amino-5-methyl-1H-pyrazole in 100 cm3 of dioxane. 73 cm3 (0.6 mol) of benzoyl chloride were added dropwise to this solution at 65° C. The temperature was brought to 80° C. and maintained for 1 hour. The solution was subsequently brought back to 10° C. A beige solid formed during the reaction was pulled dry on sintered glass and was then taken up again with stirring in 400 cm3 of methanol. The solution was filtered and the filtrate was concentrated under vacuum. A beige solid crystallized and was pulled dry on sintered glass and then washed with 50 cm3 of isopropyl ether. After drying under vacuum at 40° C., 25 g of the expected product were obtained in the form of beige crystals, the melting point of which was between 218 and 220° C.

Workup

  1. customwas brought to 80° C.
  2. temperaturemaintained for 1 hour
  3. customwas subsequently brought back to 10° C
  4. customA beige solid formed during the reaction
  5. customwas pulled dry on sintered glass
  6. filtrationThe solution was filtered
  7. concentrationthe filtrate was concentrated under vacuum
  8. customA beige solid crystallized
  9. customwas pulled dry on sintered glass
  10. washwashed with 50 cm3 of isopropyl ether
  11. customAfter drying under vacuum at 40° C.

Sources & evidence

ORD record
ord-20f8dd74ab52489bbd59e03d5c812bf7
Source dataset
uspto-grants-2000_09
Patent number
US06118008

Reaction notes

Loading…