Sulfuric Acid → HCID 12283221, compound

HRID 1861331Notes

Reaction equation

HRID 1861331 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][C:6]2([CH3:14])[CH3:13].S(=O)(=O)(O)O.[N-:20]=[N+]=[N-].[Na+]>C1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:20][CH2:7][C:6]2([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 122832145-methoxy-3,3-dimethyl-1-indanone2×

Product 1

HCID 12283221HCID 12283221, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5-methoxy-3,3-dimethyl-indane-1-one (Intermediate 16, 3.3 g, 17.4 mmol) in benzene (50 mL) was treated with concentrated sulfuric acid (10 mL) and heated to 60° C. Sodium azide (1.95 g, 30 mmol) was added in small portions and after the addition was complete, the reaction mixture was heated further for 4 h. It was then cooled, diluted with water and extracted with chloroform (×3). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound as a brown solid (3.5 g, quantitative by weight).

Workup

  1. additionafter the addition
  2. temperaturethe reaction mixture was heated further for 4 h
  3. temperatureIt was then cooled
  4. extractionextracted with chloroform (×3)
  5. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-59370dd82b0646538548aa1b52d45880
Source dataset
uspto-grants-2003_03
Patent number
US06531599B2

Reaction notes

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