Nitric Acid → HCID 178468358, compound

HRID 1407085Notes

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

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

customreached to room temperature
extractionextracted with dichloromethane
washwashed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d775e89473f9410bb35f67b029625d3d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916566B2

Reaction notes

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