Formaldehyde → 1H-Benzotriazole-1-methanol

HRID 445026

Reaktionsgleichung

Reaktionsgleichung von HRID 445026
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH2:9]=[O:10].[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1>>[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH:5][CH3:14].[OH:10][CH2:9][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1.[NH:11]1[C:3]2[CH:2]=[CH:8][CH:7]=[CH:6][C:4]=2[N:5]=[N:12]1

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 97423-FluoroanilineHCID 178418385HCID 178418385, Verbindung

Produkt 3

HCID 2241691H-Benzotriazole-1-methanolHCID 27590113-fluoro-N-methylanilineHCID 178418385HCID 178418385, Verbindung

Versuchsvorschrift

3-Fluoro-N-methylaniline was prepared from 3-fluoroaniline using a modified reductive amination. First, 1-hydroxymethylbenzotriazole was prepared by adding 37% aqueous formaldehyde to benzotriazole at 40° C. in a 1:1 ratio, then cooling to room temperature to precipitate the product. After filtration the hydroxymethylbenzotriazole (125 g) was heated to reflux in toluene with 3-fluoroaniline (92.2 g). Water was removed azeotropically using a Dean-Stark trap. After three hours, the mixture was cooled to room temperature, then refrigerated for several hours to complete precipitation. The white crystalline solid was filtered off, yielding 174.2 g (86.6%) of 1-(3-fluoroanilino)methyl)-1H-benzotriazole.

Aufarbeitung

  1. customto precipitate the product
  2. filtrationAfter filtration the hydroxymethylbenzotriazole (125 g)
  3. temperaturewas heated
  4. temperatureto reflux in toluene with 3-fluoroaniline (92.2 g)
  5. customWater was removed azeotropically
  6. temperaturethe mixture was cooled to room temperature
  7. waitrefrigerated for several hours
  8. customprecipitation
  9. filtrationThe white crystalline solid was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-4e78ed52cc4843edbcb648936f167cfe
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476280B2

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