Sulfuric Acid → HCID 21221632, compound

HRID 1457066Notes

Reaction equation

HRID 1457066 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:16][CH2:15][C:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11](N)=[CH:10][C:9]=3[C:5]=2[CH2:4]1.N([O-])=[O:19].[Na+].S(=O)(=O)(O)O.C(=O)([O-])[O-].[K+].[K+]>Cl.O>[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:16][CH2:15][C:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11]([OH:19])=[CH:10][C:9]=3[C:5]=2[CH2:4]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 9839408HCID 9839408, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21221632HCID 21221632, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 0.332 gm (1.44 mMol) N,N-dimethyl-8-amino-1,2,3,4-tetrahydro-2-dibenzofuranamine in 5 mL concentrated hydrochloric acid and 5 mL water was cooled to -10° C. To this solution was added a solution of 0.109 gm (1.58 mMol) sodium nitrite in 10 mL water dropwise. The resulting solution was stirred for 1 hour and was then added to 10 mL concentrated sulfuric acid. This mixture was stirred at reflux for 4 hours. The reaction mixture was poured over ice and the solution made basic by the addition of aqueous potassium carbonate. The solution was then extracted well with chloroform containing 10% isopropanol. The organic extracts were combined, dried over potassium carbonate and concentrated under reduced pressure. The residue was subjected to radial chromatography (silica gel, 2 mm). Fractions containing product were combined and concentrated under reduced pressure to provide 0.121 gm (36%) of the title compound as an off-white foam.

Workup

  1. stirringThis mixture was stirred
  2. temperatureat reflux for 4 hours
  3. additionThe reaction mixture was poured over ice
  4. extractionThe solution was then extracted well with chloroform containing 10% isopropanol
  5. dry with materialdried over potassium carbonate
  6. concentrationconcentrated under reduced pressure
  7. additionFractions containing product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f72e968afaea4ab695ac9dc5280b0415
Source dataset
uspto-grants-1998_12
Patent number
US05846995

Reaction notes

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