Sodium Azide → HCID 86658792, compound

HRID 2202098Notes

Reaction equation

HRID 2202098 reaction equation
[O:1]=[CH:2][C:3]#[C:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CS(C)=O>[CH:2]([C:3]1[C:4]([C:5]2[CH:6]=[CH:7][C:8]([C:9]#[N:10])=[CH:11][CH:12]=2)=[N:13][NH:14][N:15]=1)=[O:1]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 53242308HCID 53242308, compound

Product 1

HCID 86658792HCID 86658792, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-(3-oxoprop-1-ynyl)benzonitrile (500 mg, 3.22 mmol, 1.00 equiv) in DMSO (15 mL) was added NaN3 (314 mg, 4.83 mmol, 1.50 equiv) in portions. The resulting solution was stirred at room temperature for 1 h and then quenched by the addition of 1 mL of water. The resulting mixture was concentrated under vacuum and the residue was purified on a C18 flash column eluted with 0-15% of acetonitrile in water to give 130 mg (20%) of 4-(5-formyl-2H-1,2,3-triazol-4-yl)benzonitrile as a light yellow solid. LCMS (method C, ESI), RT=0.93 min, m/z=199.0 [M+1]+

Workup

  1. customquenched by the addition of 1 mL of water
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customthe residue was purified on a C18 flash column
  4. washeluted with 0-15% of acetonitrile in water

Sources & evidence

ORD record
ord-490600ee226a41819ee43f8913cac4e6
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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