Nitric Acid → HCID 21184391, compound

HRID 1385212Notes

Reaction equation

HRID 1385212 reaction equation
[O:1]=[C:2]1[C:11]2[N:12]=[C:13]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[S:14][C:10]=2[C:9](=[O:20])[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[N+:21]([O-])([OH:23])=[O:22]>S(=O)(=O)(O)O>[O:1]=[C:2]1[C:11]2[N:12]=[C:13]([C:15]3[O:16][C:17]([N+:21]([O-:23])=[O:22])=[CH:18][CH:19]=3)[S:14][C:10]=2[C:9](=[O:20])[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 10446437HCID 10446437, compound

Product 1

HCID 21184391HCID 21184391, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To 5 g (17.8 mmol) of 4,9-dihydro-4,9-dioxo-2-(furan-2-yl)naphtho[2,3-d]thiazole, one adds 20 mL of fuming nitric acid and 20 mL of concentrated sulfuric acid at room temperature. The reaction mixture is heated to reflux for 72 h; the precipitate formed is filtered through fritted glass, washed with water, and rinsed with ether. The dark yellow powder obtained is recrystallized in DMF after color removal with animal black. In this manner, 2 g of 4,9-dihydro-4,9-dioxo-2-(5-nitro-furan-2-yl)naphtho-[2,3-d]thiazole are produced in the form of a dark yellow solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 72 h
  3. customthe precipitate formed
  4. filtrationis filtered through fritted glass
  5. washwashed with water
  6. washrinsed with ether
  7. customThe dark yellow powder obtained
  8. customis recrystallized in DMF
  9. customafter color removal with animal black

Sources & evidence

ORD record
ord-6296a2f8bf154434b8dbab36925113d0
Source dataset
uspto-grants-2001_07
Patent number
US06262095B1

Reaction notes

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