Nitric Acid → HCID 67184092, compound

HRID 2380783Notes

Reaction equation

HRID 2380783 reaction equation
[CH3:1][N:2]([N:4]=[N:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([O:13][CH3:14])=[O:12])[CH3:3].S(=O)(=O)(O)O.[N+:20]([O-])([OH:22])=[O:21].[OH-].[NH4+]>O>[CH3:3][N:2]([N:4]=[N:5][C:6]1[CH:10]=[C:9]([N+:20]([O-:22])=[O:21])[S:8][C:7]=1[C:11]([O:13][CH3:14])=[O:12])[CH3:1]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 16639509HCID 16639509, compound

Product 1

HCID 67184092HCID 67184092, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 3-[(dimethylamino)diazenyl]thiophene-2-carboxylate (2 g, 9.38 mmol) was added slowly for 15 min at 0 to −5° C. to concentrated sulfuric acid (20 mL). Then concentrated nitric acid (0.54 mL, 70%, 10.7 mmol) was added to the above reaction mixture for 10 min and stirred at the same temperature for 1 h and rt for 16 h. The mixture was poured into ice cooled water and basified with ammonium hydroxide. The solution was extracted with chloroform (3×100 mL) and the combined organic layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using hexane-ethyl acetate (80:20) as eluents to give the product as a yellow color solid (450 mg, 26%), mp 128-130° C.

Workup

  1. additionThe mixture was poured into ice
  2. extractionThe solution was extracted with chloroform (3×100 mL)
  3. washthe combined organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. customevaporated the solvent
  7. customThe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-6fca64d3a1884b18955fbf65c9878219
Source dataset
uspto-grants-2012_09
Patent number
US08258119B2

Reaction notes

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