Water → N-methyl-2-nitro-5-[2-(1H-1,2,4-triazol-1-ylmethyl)-4-(trifluoromethyl)phenoxy]aniline

HRID 1081878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1081878
[N:1]1([CH2:6][C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=2[OH:17])[CH:5]=[N:4][CH:3]=[N:2]1.F[C:19]1[CH:20]=[CH:21][C:22]([N+:27]([O-:29])=[O:28])=[C:23]([CH:26]=1)[NH:24][CH3:25].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:25][NH:24][C:23]1[CH:26]=[C:19]([O:17][C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=2[CH2:6][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH:20]=[CH:21][C:22]=1[N+:27]([O-:29])=[O:28]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 229057745-fluoro-N-methyl-2-nitroanilineHCID 233631492-(1H-1,2,4-triazol-1-ylmethyl)-4-(trifluoromethyl)phenol

Produkt 1

HCID 23363127N-methyl-2-nitro-5-[2-(1H-1,2,4-triazol-1-ylmethyl)-4-(trifluoromethyl)phenoxy]anilineAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The solution of 2-(1H-1,2,4-triazol-1-ylmethyl)-4-(trifluoromethyl)phenol (1.0 g) from Example 62, 5-fluoro-N-methyl-2-nitroaniline (700 mg) and K2CO3 (0.57 g) in DMF (10 ml) was heated at 100° C. for 90 minutes. After the solution was left to stand at room temperature, water was added to the solution, the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by chromatography on a silica gel column (methylene chloride:methanol=99:1), to give the title compound (960 mg; 59%).

Aufarbeitung

  1. waitAfter the solution was left
  2. customto stand at room temperature
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by chromatography on a silica gel column (methylene chloride:methanol=99:1)

Quellen und Nachweise

ORD-Eintrag
ord-ebbca986753145b8bfafa07fb9be7a92
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587392

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