Cyanuric chloride → 4-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carbonitrile

HRID 2079833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2079833
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])=[N:5][N:4]=[C:3]1[C:17]12[CH2:24][CH2:23][C:20]([C:25]([NH2:27])=O)([CH2:21][CH2:22]1)[CH2:19][CH2:18]2.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:15])([F:14])[F:16])=[N:5][N:4]=[C:3]1[C:17]12[CH2:22][CH2:21][C:20]([C:25]#[N:27])([CH2:23][CH2:24]1)[CH2:19][CH2:18]2

Komponenten

4

Edukt 2

HCID 7954Cyanuric chlorideHCID 207550404-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carboxamide

Produkt 1

HCID 671194154-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of carboxamide 1-E (0.64 g, 1.7 mmol) and cyanuric chloride (0.47 g, 2.53 mmol) in DMF (15 ml) was stirred at room temperature under a nitrogen atmosphere. After 2 h, DMF was removed in vacuo and the solid was redissolved in methylene chloride (100 ml). This solution was washed with saturated aqueous sodium bicarbonate and brine, dried (Na2SO4), and stripped to give 1-F as a pale yellow solid. MS (ESI+)=361.3 (M+1); 1H NMR (500 MHz, CDCl3): δ2.15 (6H, m), 2.22 (6H, m), 3.47 (3H, s), 7.51 (1H, m), 7.72 (2H, m), 7.87 (1H, m) ppm.

Aufarbeitung

  1. customDMF was removed in vacuo
  2. dissolutionthe solid was redissolved in methylene chloride (100 ml)
  3. washThis solution was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried (Na2SO4)

Quellen und Nachweise

ORD-Eintrag
ord-d486b7b5c3654a1080e6ba309932da2c
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932280B2

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