Benzyl azide → 1-Phenylmethyl-4-(2,4,6-trimethylphenyl)-5-aminotriazole

HRID 2243841Notes

Reaction equation

HRID 2243841 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[CH2:4][C:5]#[N:6].[CH2:13]([N:20]=[N+:21]=[N-:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[K+]>O1CCCC1.O>[C:14]1([CH2:13][N:20]2[C:5]([NH2:6])=[C:4]([C:3]3[C:7]([CH3:12])=[CH:8][C:9]([CH3:11])=[CH:10][C:2]=3[CH3:1])[N:22]=[N:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 12152Benzyl azideHCID 5206982,4,6-TrimethylphenylacetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 154869821-Phenylmethyl-4-(2,4,6-trimethylphenyl)-5-aminotriazoleYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,4,6-trimethylbenzyl cyanide (1.0 g, 6.3 mmol), benzyl azide (0.92 g, 6.9 mmol) and potassium t-butoxide (0.78 g, 6.9 mmol) in tetrahydrofuran (10 mL) was stirred at ambient temperature for 2.5 days. The resulting suspension was diluted with water and extracted three times with ethyl acetate. The combined organic layers were dried over MgSO4 and filtered. Solvent was removed in vacuo to give a brown oil. Trituration with ether and filtration afforded a yellow solid (1.12 g, 61% yield): NMR (CDCl3, 300 MHz): 7.60-7.30 (m, 5H), 7.30-7.20 (m, 2H), 5.50 (s, 2H), 3.18 (br s, 2H), 2.30 (s, 3H), 2.10 (s, 6H); CI-MS: 293 (M+H).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customSolvent was removed in vacuo
  5. customto give a brown oil
  6. filtrationTrituration with ether and filtration

Sources & evidence

ORD record
ord-201e9c799d6e49f9a844bd4524a0038a
Source dataset
uspto-grants-2010_03
Patent number
US07678793B2

Reaction notes

Loading…