Sodium Azide → HCID 20645038, compound

HRID 323769Notes

Reaction equation

HRID 323769 reaction equation
CS(O[CH2:6][C@@H:7]1[CH2:9][C@@H:8]1[C:10]1[C:15]2[CH2:16][CH2:17][O:18][C:14]=2[CH:13]=[CH:12][CH:11]=1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C)C=O.C(Cl)Cl>[O:18]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C@H:8]3[CH2:9][C@H:7]3[CH2:6][N:19]=[N+:20]=[N-:21])[C:15]=2[CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 20645039HCID 20645039, compound

Product 1

HCID 20645038HCID 20645038, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (cis)-[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methyl methane sulfonate (5.0 mmol) and sodium azide (10.0 mmol) in 100 mL of dimethylformamide was heated at 70° C. for 1 h. The reaction mixture was allowed to cool to room temperature and stirred overnight. The crude reaction mixture was then diluted with CH2Cl2 (100×mL) and washed sequentially with water (3×100 mL) and then brine (1×100 mL). The organic phase was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to provide 1.1 g of the desired product as an oil (quantitative yield).

Workup

  1. customThe crude reaction mixture
  2. washwashed sequentially with water (3×100 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c3b709365c0486a88d68fd91b5d8b35
Source dataset
uspto-grants-2001_04
Patent number
US06214869B1

Reaction notes

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