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Dichloromethane → 3,8-Diphenyl-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)imidazo[1,2-d][1,2,4]triazine

HRID 396152
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Reaktionsgleichung

Reaktionsgleichung von HRID 396152
[C:1]1([C:7]2[N:11]3[CH:12]=[N:13][N:14]=[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:10]3=[N:9][C:8]=2[OH:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:25][C:26]1[N:27]([CH3:31])[N:28]=[CH:29][N:30]=1.[H-].[Na+].C(Cl)Cl>CN(C)C=O>[C:1]1([C:7]2[N:11]3[CH:12]=[N:13][N:14]=[C:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:10]3=[N:9][C:8]=2[O:22][CH2:25][C:26]2[N:27]([CH3:31])[N:28]=[CH:29][N:30]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 111853273,8-Diphenylimidazo[1,2-d][1,2,4]triazin-2-olHCID 222853325-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochloride

Produkt 1

HCID 99519603,8-Diphenyl-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)imidazo[1,2-d][1,2,4]triazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3,8-diphenylimidazo[1,2-d][1,2,4]triazin-2-ol (500 mg, 1.74 mmol) and 3-chloromethyl-2-methyl-2H-[1,2,4]triazole hydrochloride (320 mg, 1.91 mmol) in anhydrous N,N-dimethylformamide under an atmosphere of nitrogen was added sodium hydride (153 mg of a 60% dispersion in oil, 3.8 mmol). The reaction mixture was stirred at room temperature for 72 h. The mixture was partitioned between EtOAc (80 ml) and water (150 ml), the organic layer was separated, and the aqueous layer extracted with a further two portions of EtOAc (80 ml). The combined EtOAc layers were washed with saturated NaCl solution (100 ml), separated, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 2% MeOH in CH2Cl2+0.5% NH3), and the product recrystallised from CH2Cl2 to afford 235 mg (0.6 mmol, 35%) as a white solid. (Found: C, 63.66; H, 4.23; N, 24.54; C21H17N7O.0.5H2O.0.07CH2Cl2 requires C, 63.47; H, 4.59; N, 24.59%); m.p. 179° C. (from CH2Cl2); δH (400 MHz; CDCl3) 3.95 (3H, s, NCH3), 5.75 (2H, s, OCH2), 7.46 (1H, t, J 7.3, aromatic), 7.52-7.60 (5H, m, aromatics), 7.63 (2H, d, J 7.6, aromatics), 7.88 (1H, s, triazole H5), 8.57-8.65 (2H, br m, aromatics), 9.43 (1H, s, imidazotriazine H5); m/z (ES+) 384 (M++H, 100%).

Aufarbeitung

  1. customThe mixture was partitioned between EtOAc (80 ml) and water (150 ml)
  2. customthe organic layer was separated
  3. extractionthe aqueous layer extracted with a further two portions of EtOAc (80 ml)
  4. washThe combined EtOAc layers were washed with saturated NaCl solution (100 ml)
  5. customseparated
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography (SiO2; 2% MeOH in CH2Cl2+0.5% NH3)
  9. customthe product recrystallised from CH2Cl2
  10. customto afford 235 mg (0.6 mmol, 35%) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-aedd9fe61d034bacad7bf8dcc4e96300
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06608062B1

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