Sulfuric Acid → HCID 20212201, compound

HRID 1906524Notes

Reaction equation

HRID 1906524 reaction equation
[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([Cl:14])=[CH:4][CH:3]=1.[N+]([O-])([O-])=O.[Na+].NC(N)=O.[N-:24]=[N+:25]=[N-].[Na+].[S:28](=[O:32])(=[O:31])([OH:30])[OH:29]>O>[S:28]([OH:32])([OH:31])(=[O:30])=[O:29].[N:1]([C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([Cl:14])=[CH:4][CH:3]=1)=[N+:24]=[N-:25]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 1176UreaHCID 24268Sodium NitrateHCID 33557Sodium AzideHCID 13338332HCID 13338332, compound

Product 1

HCID 20212201HCID 20212201, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 630 mg (3 mmol) of 9-amino-6-chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in 2 ml of concentrated sulfuric acid and 10 ml of water was added 280 mg (4 mmol) of sodium nitrate in 5 ml of water. The mixture was stirred in an ice bath during addition, then, allowed to warm to room temperature. After stirring at room temperature for one hour, 60 mg of urea was added to destroy excess nitrous acid. To this solution was added 330 mg (5 mmol) of sodium azide and the resulting solution stirred at room temperature. Nitrogen was evolved and a white precipitate formed. After stirring overnight, this was removed by filtration, stirred with a small amount of cold ethanol, filtered again and washed with ether to leave 545 mg (58%) of slightly off-white crystals, 9-azido-6-chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine sulfate. This material was crystallized from ethanol to give 390 mg as a slightly yellow crystalline solid, m.p. 71°-75° (dec), IR and NMR spectra support structure.

Workup

  1. stirringAfter stirring at room temperature for one hour
  2. customto destroy excess nitrous acid
  3. stirringthe resulting solution stirred at room temperature
  4. customa white precipitate formed
  5. stirringAfter stirring overnight
  6. customthis was removed by filtration
  7. stirringstirred with a small amount of cold ethanol
  8. filtrationfiltered again
  9. washwashed with ether

Sources & evidence

ORD record
ord-ac44f39127a243f78450d9c34e1dc776
Source dataset
uspto-grants-1987_03
Patent number
US04652642

Reaction notes

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