1H-Benzotriazole-1-carboxaldehyde → HCID 86617531, Verbindung

HRID 554097

Reaktionsgleichung

Reaktionsgleichung von HRID 554097
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH2:13].[CH:14](N1C2C=CC=CC=2N=N1)=[O:15]>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][CH:14]=[O:15]

Komponenten

4

Edukt 2

HCID 5767401H-Benzotriazole-1-carboxaldehydeHCID 52242072-Chloro-3-(trifluoromethyl)benzylamine

Produkt 1

HCID 86617531HCID 86617531, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (1.05 g, 5 mmol) in anhydrous tetrahydrofuran (10 ml) was added dropwise to a solution of N-formyl benzotriazole (0.772 g, 5.25 mmol) in anhydrous tetrahydrofuran (10 ml). The reaction was stirred at 22° C. for 18 hrs then reduced in vacuo and the residue partitioned between dichloromethane (75 ml) and 2N aqueous sodium hydroxide (40 ml). The organic layer was separated and extracted with 2N aqueous sodium hydroxide (40 ml). The organic layer was passed through a hydrophobic frit and reduced in vacuo to give a white solid. The crude product was purified by automated flash silica column chromatography (Biotage SP4), eluting with a solvent gradient of 0-10% ethyl acetate in dichloromethane, to give {[2-chloro-3-(trifluoromethyl)phenyl]methyl}formamide as a white solid.

Aufarbeitung

  1. customthe residue partitioned between dichloromethane (75 ml) and 2N aqueous sodium hydroxide (40 ml)
  2. customThe organic layer was separated
  3. extractionextracted with 2N aqueous sodium hydroxide (40 ml)
  4. customto give a white solid
  5. customThe crude product was purified by automated flash silica column chromatography (Biotage SP4)
  6. washeluting with a solvent gradient of 0-10% ethyl acetate in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b3be5526566349b28bd9d43bbc96de7f
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048907B2

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