Nitric Acid → HCID 69061392, compound

HRID 227627Notes

Reaction equation

HRID 227627 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH3:18])[CH:5]=[CH:6][CH:7]=1.[N+:19]([O-])([OH:21])=[O:20].C([O-])([O-])=O.[Na+].[Na+]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH3:18])[CH:5]=[CH:6][C:7]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 69061324HCID 69061324, compound

Product 1

HCID 69061392HCID 69061392, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A 0° C. suspension of Example 143A (2.13 g, 7.74 mmol) in concentrated H2SO4 (15 mL) was treated dropwise over 3 minutes with a solution of fuming nitric acid (0.38 mL) in concentrated H2SO4 (5 mL). The mixture was stirred for 30 minutes while warming to room temperature, poured onto ice, adjusted to pH 7 with solid Na2CO3, and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated to provide 2.31 g (93% yield) of the desired product. MS(ESI(+)) m/e 321 (M+H)+.

Workup

  1. additionpoured onto ice
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-47ad4d5c86b143f586e271bc930ae638
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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