Sodium Azide → 1-(4-Cyanophenyl)-5-azido-1-pentyne

HRID 21612Notes

Reaction equation

HRID 21612 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]#[C:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C)C=O.O>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:10]#[C:9][CH2:8][CH2:7][CH2:6][N:19]=[N+:20]=[N-:21])=[CH:12][CH:13]=1)#[N:18]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 194268975-(4-Cyanophenyl)-4-pentynyl methanesulfonate

Product 1

HCID 156429951-(4-Cyanophenyl)-5-azido-1-pentyneYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of step B (13.40 g, 50.9 mmol) in dimethylformamide (35 mL) was added NaN3 (16.5 g, 255 mmol). The reaction was stirred at room temperature for 18 hours then at 60° C. for 2 hours, cooled to room temperature, diluted with water (400 mL) and extracted with ethyl acetate. The organic layer was washed with water (2×) then with brine and dried (Na2SO4). Evaporation under reduced pressure afforded 10.70 g (100%) of product as a tan oil.

Workup

  1. waitat 60° C. for 2 hours
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water (2×)
  5. dry with materialwith brine and dried (Na2SO4)
  6. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-6f1438d31ddb4fab88a1d2f419016406
Source dataset
uspto-grants-1995_06
Patent number
US05424334

Reaction notes

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