Nitric Acid → 4-Nitro-5-propionamido-1-(2,3,4-trichlorophenyl)-pyrazole

HRID 65385Notes

Reaction equation

C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[C:12]([NH:16][C:17]1[N:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[C:23]=2[Cl:30])[N:20]=[CH:19][CH:18]=1)(=[O:15])[CH2:13][CH3:14]>C(O)(=O)C>[N+:8]([C:18]1[CH:19]=[N:20][N:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[C:23]=2[Cl:30])[C:17]=1[NH:16][C:12](=[O:15])[CH2:13][CH3:14])([O-:11])=[O:9]

Participants

Conditions

Temperature: 25 °C

Procedure

2 ml (2.17 g/0.021 mol) of acetic anhydride and then 0.9 ml (1.3 g/0.02 mol) of 98% strength nitric acid are added in succession to 6.4 g (0.02 mol) of 5-propionamido-1-(2,3,4-trichlorophenyl)-pyrazole in 20 ml of glacial acetic acid at 10° C. When the addition is complete, the mixture is stirred for 16 hours at 25° C. To work up the mixture, it is evaporated down in vacuo, the residue is taken up in 20 ml of diethyl ether, the solution is washed three times with a total of 50 to 100 ml of concentrated sodium bicarbonate solution and twice with 50 ml of saturated sodium chloride solution, the solvent is removed in a vacuum from a water pump, and the solid residue is washed with a small amount of water and dried in a high vacuum at 30° C. to 40° C. 5.5 g (76% of theory) of 4-nitro-5-propionamido-1-(2,3,4-trichlorophenyl)-pyrazole of melting point 79°-81° C. are obtained.

Workup

additionWhen the addition
customis evaporated down in vacuo
washthe solution is washed three times with a total of 50 to 100 ml of concentrated sodium bicarbonate solution
customtwice with 50 ml of saturated sodium chloride solution, the solvent is removed in a vacuum from a water pump
washthe solid residue is washed with a small amount of water
customdried in a high vacuum at 30° C. to 40° C

Sources & evidence

ORD record: ord-b63ac5e8dc2241d697cca47bea120cf9
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04614533

Reaction notes

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