Hydrochloric Acid → HCID 67459883, Verbindung

HRID 2238512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2238512
O1CCCC1.B.[CH3:7][C:8]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH2:12])=O.[ClH:21]>O1CCCC1>[ClH:21].[CH3:7][C:8]1[C:16]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:14]=[CH:13][C:9]=1[CH2:10][NH2:12]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 27755662-methyl-3-(trifluoromethyl)benzamide

Produkt 1

HCID 67459883HCID 67459883, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Borane tetrahydrofuran (1M, 39.4 ml, 39.4 mmol) was added to a solution of 2-methyl-3-trifluoromethyl benzamide (2 g, 9.85 mmol) in tetrahydrofuran (75 ml) and stirred at 70° C. for 5 hrs. LCMS showed incomplete reaction so heating at 70° C. under argon was continued overnight and then for a further 5 hrs following this. The reaction mixture was treated with 2N aqueous hydrogen chloride and stirred at 100° C. for 4 hrs and then left to cool over the weekend. The mixture was reduced to dryness undervacuum and then partitioned between dichloromethane and 2N aqueous sodium hydroxide. The organic layer was separated using a hydrophobic frit and reduced to give a residue which was purified by flash silica column chromatography (eluting with 0-5% 2N ammonia/methanol in dichloromethane). The solvent was evaporated and the residue taken up in diethyl ether and treated with 1M ethereal hydrogen chloride. The solid that precipitated was collected by filtration and this was then triturated with dichloromethane and after filtration 2-Methyl-3-(trifluoromethyl)phenyl]methyl}amine hydrochloride (1.4 g) was obtained as a white solid.

Aufarbeitung

  1. customreaction
  2. temperatureso heating at 70° C. under argon
  3. waitwas continued overnight
  4. waitfor a further 5 hrs following
  5. stirringstirred at 100° C. for 4 hrs
  6. waitleft
  7. temperatureto cool over the weekend
  8. custompartitioned between dichloromethane and 2N aqueous sodium hydroxide
  9. customThe organic layer was separated
  10. customto give a residue which
  11. customwas purified by flash silica column chromatography (eluting with 0-5% 2N ammonia/methanol in dichloromethane)
  12. customThe solvent was evaporated
  13. additiontreated with 1M ethereal hydrogen chloride
  14. customThe solid that precipitated
  15. filtrationwas collected by filtration
  16. customthis was then triturated with dichloromethane
  17. filtrationafter filtration 2-Methyl-3-(trifluoromethyl)phenyl]methyl}amine hydrochloride (1.4 g)
  18. customwas obtained as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-028be83d6da54a38aef9725b46b7bad5
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718693B2

Notizen zur Reaktion

Wird geladen…