Nitric Acid → HCID 13849582, compound

HRID 1906099Notes

Reaction equation

HRID 1906099 reaction equation
[CH:1]([C:4]1([CH3:23])[C:8](=[O:9])[NH:7][C:6]([C:10]2[N:15]=[C:14]3[S:16][CH:17]=[CH:18][C:13]3=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[N:5]1)([CH3:3])[CH3:2].[N+:24]([O-])([OH:26])=[O:25].C([O-])(O)=O.[Na+]>OS(O)(=O)=O>[CH:1]([C:4]1([CH3:23])[C:8](=[O:9])[NH:7][C:6]([C:10]2[N:15]=[C:14]3[S:16][CH:17]=[C:18]([N+:24]([O-:26])=[O:25])[C:13]3=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 13752461HCID 13752461, compound

Product 1

HCID 13849582HCID 13849582, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
3 °C

Procedure

Methyl 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)thieno[2,3-b]pyridine-5-carboxylate (3.94 g, 0.0119 mol) is dissolved in 200 mL concentrated H2SO4 at room temperature. While cooling to 3° C. in an ice bath, 1.5 mL (0.024 mol) concentrated HNO3 is added, then the mixture is allowed to warm to room temperature. After three hours, the reaction mixture is poured onto ice, neutralized with solid NaHCO3 to pH 6 and is extracted with methylene chloride. The extract is filtered, then dried over sodium sulfate, refiltered and concentrated to a yield solid weighing 4.33 g (97%), which upon crystallization from methanol water has mp 201°-202.5° C.

Workup

  1. temperatureto warm to room temperature
  2. additionthe reaction mixture is poured onto ice
  3. extractionis extracted with methylene chloride
  4. filtrationThe extract is filtered
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to a yield solid
  7. customupon crystallization from methanol water

Sources & evidence

ORD record
ord-15ff52fb382b4455be219a4552bc2d41
Source dataset
uspto-grants-1987_03
Patent number
US04650514

Reaction notes

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