Sodium Azide → HCID 178423506, compound

HRID 133008Notes

Reaction equation

HRID 133008 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][N:7]=[C:8]3[C:13]=2[C:12]=1[C:11](=[O:14])[C:10]1[CH:15]=[CH:16][CH:17]=[CH:18][C:9]3=1.[N-:19]=[N+]=[N-].[Na+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][N:7]=[C:8]3[C:9]4[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=4[C:11](=[O:14])[NH:19][C:12]=1[C:13]=23

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 21064953HCID 21064953, compound

Product 1

HCID 178423506HCID 178423506, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 15 g of 5-methyl-2,6-dihydrodibenzo[cd,g]indazol-6-one prepared in Example 25-b in 70 ml concentrated sulfuric acid was added 12.5 g of sodium azide [CAS No. 26628-22-8], followed by stirring at room temperature for 30 hours. The reaction mixture was poured onto 700 ml of ice-water, the precipitated powder was collected by filtration and dried in vacuo. The resulting powder was dissolved in a solvent mixture of dimethylformamide-ethyl acetate, sequentially washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was recrystallized from dimethylformamide-ethyl acetate, to give 6.59 g of the title compound as ocher yellow crystals.

Workup

  1. filtrationthe precipitated powder was collected by filtration
  2. customdried in vacuo
  3. dissolutionThe resulting powder was dissolved in a solvent mixture of dimethylformamide-ethyl acetate
  4. washsequentially washed with saturated aqueous sodium hydrogencarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was recrystallized from dimethylformamide-ethyl acetate

Sources & evidence

ORD record
ord-0a1eea6307da46b6b20bca95d5afec62
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

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