Dimethylformamide → 4-[(3-amino-1H-1,2,4-triazol-1-yl)methyl]benzonitrile

HRID 2063640Notes

Reaction equation

HRID 2063640 reaction equation
[NH2:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.[H-].[Na+].BrC[C:11]1[C:12]([C:17]#[N:18])=[CH:13][CH:14]=[CH:15][CH:16]=1.[CH3:19]N(C=O)C>>[NH2:1][C:2]1[N:6]=[CH:5][N:4]([CH2:19][C:15]2[CH:16]=[CH:11][C:12]([C:17]#[N:18])=[CH:13][CH:14]=2)[N:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 895992-(Bromomethyl)benzonitrileHCID 178418311HCID 178418311, compound

Product 1

HCID 609117294-[(3-amino-1H-1,2,4-triazol-1-yl)methyl]benzonitrileYield 32.6%

Procedure

3-Amino-1,2,4-triazole (883 mg, 10.5 mmol) was dissolved in DMF (20 ml) under argon atmosphere, sodium hydride (55%, 436 mg, 10 mmol) added at rt in small portions and stirred at rt for 1 hour. To the reaction mixture alpha bromotolunitrile (1.96 g, 10 mmol) was added and stirred at rt overnight. TLC: finished: The reaction mixture was poured onto water, extracted with ethyl acetate and water, the organic layers combined, dried over Na2SO4, filtered and the solvents evaporated. Purification by flash chromatography with CH2Cl2/MeOH 100:0 to 90:10; 35 min over a 100 g silica-gel column gave 650 mg (yield: 32.6%) white solid. MS ISP (m/e): 200.2 (100) [(M+H)+].

Workup

  1. stirringstirred at rt overnight
  2. additionThe reaction mixture was poured onto water
  3. extractionextracted with ethyl acetate and water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents evaporated
  7. customPurification by flash chromatography with CH2Cl2/MeOH 100:0 to 90:10

Sources & evidence

ORD record
ord-92a74c85a81949bdbf76e2c034788a8f
Source dataset
uspto-grants-2012_10
Patent number
US08288403B2

Reaction notes

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