Nitric Acid → HCID 178468326, compound

HRID 1805545Notes

Reaction equation

HRID 1805545 reaction equation
[CH3:1][S:2]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])=[O:3].P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:20]([O-])=O.[Na+].C([O-])(=O)C.[K+].[C:29]([CH2:32][C:33](=[O:35])[CH3:34])(=[O:31])[CH3:30]>O.C(O)C>[CH3:1][S:2]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][N:20]=[C:32]([C:33](=[O:35])[CH3:34])[C:29](=[O:31])[CH3:30])=[O:3]

Participants

9

Reactant 6

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 31261AcetylacetoneHCID 517044Potassium AcetateHCID 129130762-(methylsulfinyl)benzenamineHCID 23668193Sodium Nitrite

Product 1

HCID 178468326HCID 178468326, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(Methylsulfinyl)aniline (0.50 g, 3.22 mmol) was added to a solution of 3 mL of phosphoric acid (85%) and 2 mL of nitric acid (65%) at −6° C., followed by sodium nitrite (0.27 g, 3.87 mmol) in 2 mL of water dropwise at 0° C., and the mixture was stirred at 0° C. for 30 min. Then, to the reaction mixture was added dropwise a mixture of potassium acetate (0.95 g, 9.66 mmol) and acetylacetone (0.42 g, 4.19 mmol) in 80 mL of ethanol and 48 mL of water. The mixture was stirred at room temperature overnight, filtered, washed with water, EtOH/H2O (1/1) and hexane, and dried to give the title compound (0.66 g, 77% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.07 (3H, s), 2.55 (3H, s), 2.64 (3H, s), 7.29-7.87 (4H, m), 15.06 (1H, s).

Workup

  1. additionThen, to the reaction mixture was added dropwise
  2. stirringThe mixture was stirred at room temperature overnight
  3. filtrationfiltered
  4. washwashed with water, EtOH/H2O (1/1) and hexane
  5. customdried

Sources & evidence

ORD record
ord-9cbd3557e3334911b068435bebb860e4
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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