Sodium Azide → HCID 86086990, compound

HRID 656325Notes

Reaction equation

HRID 656325 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][C:9]2([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[O:12]2)[CH2:8][CH2:7]1)(=O)=O.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[N:21]([CH:6]1[CH2:11][CH2:10][C:9]2([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[O:12]2)[CH2:8][CH2:7]1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86602510HCID 86602510, compound

Product 1

HCID 86086990HCID 86086990, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-oxo-3H-spiro[2-benzofuran-1,1′-cyclohexan]-4′-yl methanesulfonate (120 mg, 0.40 mmol), sodium azide (263 mg, 4.05 mmol) in DMF (2.0 mL) was maintained at 80° C. overnight. After cooling, it was quenched with sat'd NH4Cl solution, then extracted with ethyl acetate. The extract was washed with water twice, brine once, and dried over anhydrous sodium sulfate. After filtration the filtrate was concentrated to yield 90 mg of 4′-azido-3H-spiro[2-benzofuran-1,1′-cyclohexan]-3-one (yield: 91%).

Workup

  1. temperatureAfter cooling
  2. customit was quenched with sat'd NH4Cl solution
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water twice
  5. dry with materialbrine once, and dried over anhydrous sodium sulfate
  6. filtrationAfter filtration the filtrate
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-e8b33cc89be44cdabf500cd7299fb50c
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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