Sodium Bicarbonate → 1,3-Diazaazulene

HRID 1194295

Reaction equation

HRID 1194295 reaction equation
S[C:2]1[N:3]=[C:4]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=[C:5]2[N:6]=1.C(=O)(O)[O-].[Na+]>[N+]([O-])(O)=O>[N:3]1[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7][C:5]2=[N:6][CH:2]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178527782HCID 178527782, compound

Product 1

HCID 6380091,3-Diazaazulene

Reagents, catalysts & solvents 1

HCID 944Nitric AcidSolvent

Procedure

With reference to Journal of the American Chemical Society, vol. 76, pages 3352 and 3353 (1954), 23 g of 2-mercaptocycloheptimidazole as synthesized in Synthetic example 1 (b) was added to 210 ml of 10% nitric acid, and stirred with heating to the inner temperature of 80° to 90° C. for one hour. The reaction solution was neutralized with sodium bicarbonate and extracted with chloroform (250 ml×2). The chloroform layer was dried over anhydrous sodium sulfate and concentrated to 50 ml under reduced pressure, and then 200 ml of hexane was added. Deposited crystals were collected by filtration and dried.

Workup

  1. temperaturewith heating to the inner temperature of 80° to 90° C. for one hour
  2. extractionextracted with chloroform (250 ml×2)
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated to 50 ml under reduced pressure
  5. addition200 ml of hexane was added
  6. filtrationDeposited crystals were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-25bb50e9cc084d5995ba5bdafc42784e
Source dataset
uspto-grants-1989_03
Patent number
US04814265

Linked notes

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