Sulfuric Acid → 6-Acetylaminocyclopenta[f][2,1,3]benzoxadiazole

HRID 1739805Notes

Reaction equation

HRID 1739805 reaction equation
N([O-])=O.[Na+].[C:5]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][C:13]([N+:19]([O-:21])=O)=[C:14]([NH2:18])[CH:15]=2)[CH2:10]1)(=[O:7])[CH3:6].S(=O)(=O)(O)O.[N-]=[N+]=[N-].[Na+]>C(O)(=O)C.O>[C:5]([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:15][C:14]3[C:13](=[CH:12]2)[NH:19][O:21][N:18]=3)[CH:17]=1)(=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 218375442-Acetylamino-5-amino-6-nitroindanHCID 23668193Sodium Nitrite

Product 1

HCID 218375316-Acetylaminocyclopenta[f][2,1,3]benzoxadiazole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

At 0° C., 0.46 g (6.6 mmol) of NaNO2, and then 1.4 g (6 mmol) of the product of Step 1 dissolved in 10 ml of acetic acid, are added to 3 ml of sulphuric acid. After 15 minutes at 0° C., the mixture is poured onto 20 g of ice. The solution so obtained is poured dropwise into a vigorously stirred solution of 600 mg (9.2 mmol) of sodium azide in 12 ml of water. The whole is stirred for 10 minutes at room temperature and extracted 3 times with 40 ml of CH2Cl2 each time. The organic phases are washed with an aqueous 10% sodium carbonate solution, dried over MgSO4 and filtered and 100 ml of dry toluene are added. The methylene chloride is evaporated off and the toluene solution so obtained is heated at reflux for 3 hours.

Workup

  1. customThe solution so obtained
  2. extractionextracted 3 times with 40 ml of CH2Cl2 each time
  3. washThe organic phases are washed with an aqueous 10% sodium carbonate solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. addition100 ml of dry toluene are added
  7. customThe methylene chloride is evaporated off
  8. customthe toluene solution so obtained
  9. temperatureis heated
  10. temperatureat reflux for 3 hours

Sources & evidence

ORD record
ord-6398e084e9784a14a6159eea2074c525
Source dataset
uspto-grants-1999_10
Patent number
US05968954

Reaction notes

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