Nitric Acid → HCID 118511093, compound

HRID 1478211Notes

Reaction equation

HRID 1478211 reaction equation
[CH:1]1([N:7]2[C:11](=[O:12])[CH:10]=[C:9]([CH3:13])[N:8]2[CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:15]([O-])([OH:17])=[O:16]>FC(F)(F)C(O)=O>[CH:1]1([N:7]2[C:11](=[O:12])[C:10]([N+:15]([O-:17])=[O:16])=[C:9]([CH3:13])[N:8]2[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 204640012-Cyclohexyl-1,2-dihydro-1,5-dimethyl-3H-pyrazol-3-one

Product 1

HCID 118511093HCID 118511093, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

To trifluoroacetic acid (1940 mL) cooled to −15° C. was added 2-cyclohexyl-1,5-dimethyl-1H-pyrazol-3(2H)-one (535 g, 2231 mmol) and the reaction mixture was cooled to 0° C. Nitric acid 90% (211 mL, 4461 mmol) was added dropwise over 90 minutes maintaining the temperature below 15° C. and the reaction mixture was stirred for 30 minutes at 10° C. The resulting mixture was slowly poured into ice water (8 L) and stirred for 30 minutes. The solid was collected by filtration and washed with water (2×2 L), saturated sodium bicarbonate solution (1×2 L), water (2×2 L), TBME (3×2 L) and heptane (2×2 L). The isolated solid was dried in the vacuum oven to afford the title compound;

Workup

  1. temperaturemaintaining the temperature below 15° C.
  2. stirringstirred for 30 minutes
  3. filtrationThe solid was collected by filtration
  4. washwashed with water (2×2 L), saturated sodium bicarbonate solution (1×2 L), water (2×2 L), TBME (3×2 L) and heptane (2×2 L)
  5. customThe isolated solid was dried in the vacuum oven

Sources & evidence

ORD record
ord-2afc52153e7a436dbcc415e00302bc5d
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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