Sodium Azide → HCID 10487846, compound

HRID 604468Notes

Reaction equation

HRID 604468 reaction equation
[O:1]=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].[N-:12]=[N+:13]=[N-:14].[Na+].[Cl-].C([NH+](CC)CC)C>C1(C)C=CC=CC=1>[C:6]1([C:2](=[O:1])[CH2:3][C:4]2[N:5]=[N:12][NH:13][N:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 64799BenzoylacetonitrileHCID 12698378Triethylazanium chloride

Product 1

HCID 10487846HCID 10487846, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Oxo-3-phenyl-propionitrile (6.5 g, 45 mmol), sodium azide (3.3 g, 50 mmol) and triethylammonium chloride (6.7 g, 50 mmol) were stirred in dry toluene (100 mL) under argon at 90° C. for 18 h. A two-phase system was formed. The reaction mixture was cooled and extracted with NaOH (2M, 2×50 mL). The aqueous solution was poured into hydrochloric acid (4M, 200 mL) and the crude product precipitated and was filtered off and recrystalliced from acetonitrile. Yield: 74%.

Workup

  1. customA two-phase system was formed
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with NaOH (2M, 2×50 mL)
  4. additionThe aqueous solution was poured into hydrochloric acid (4M, 200 mL)
  5. customthe crude product precipitated
  6. filtrationwas filtered off

Sources & evidence

ORD record
ord-c178d8d8e3ba40bbbf46d3b38c78e2b1
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

Loading…