Nitric Acid → HCID 178468358, compound

HRID 1624566Notes

Reaction equation

HRID 1624566 reaction equation
[CH3:1][S:2]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:21]([O-])=O.[Na+].[CH3:25][C:26](=[O:31])[CH2:27][C:28](=[O:30])[CH3:29].C([O-])(=O)C.[K+].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[CH3:1][S:2]([C:5]1[CH:11]=[CH:10][C:8]([NH:9][N:21]=[C:27]([C:26](=[O:31])[CH3:25])[C:28](=[O:30])[CH3:29])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

9

Reactant 7

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 10340Sodium CarbonateHCID 31261AcetylacetoneHCID 796174-(Methylsulfonyl)anilineHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468358HCID 178468358, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-6 °C

Procedure

4-(Methylsulfonyl)aniline (500 mg, 2.92 mmol) was added to a solution of 3 mL of phosphoric acid (85%) and 2 mL of nitric acid (65%) at −6° C. When the mixture reached to room temperature it was cooled to −6° C. and solid sodium nitrite (201 mg, 2.92 mmol) was added during 10 min. Small pieces of ice (50 g) were added into the solution. The mixture was added at 0° C. to a suspension of corresponding 2,4-pentanedione (292 mg, 2.92 mmol) and potassium acetate (20 g) in ethanol (250 mL). The solution was stirred for 15 min, added to 250 mL of saturated Na2CO3 aqueous solution, extracted with dichloromethane, washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to give 3-{[4-(methylsulfonyl)phenyl]hydrazono}pentane-2,4-dione (780 mg, 95%).

Workup

  1. customreached to room temperature
  2. extractionextracted with dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c11d967659e34698bbcc26ac24a7a836
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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