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

HRID 10235

Reaktionsgleichung

Reaktionsgleichung von HRID 10235
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d57d259249774992a4044291bddceda3
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094782B1

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