Benzylamine → N-Benzyl-6-chloro-nicotinamide

HRID 380756

Reaktionsgleichung

Reaktionsgleichung von HRID 380756
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][N:7]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:15]([NH:22][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:6]([Cl:5])=[N:7][CH:8]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

7

Edukt 4

HCID 7504BenzylamineHCID 24386Thionyl ChlorideHCID 792226-Chloronicotinic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 857488N-Benzyl-6-chloro-nicotinamideAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3.5 ml (47.6 mMol) Thionylchloride and 50 □l DMF were added to a suspension of 5.0 g (31.7 mMol) 6-chloronicotinic acid in 50 ml toluene and the reaction mixture was heated at 80° C. for 2 hours. The solvent and excess thionyl chloride were removed under reduced pressure and the residue was dissolved in 50 ml dichloromethane. After cooling to 0° C., 10.4 ml (95.2 mMol) benzylamine were added over 20 minutes and after 30 minutes further stirring at room temperature, the reaction mixture was poured onto 50 ml aqueous saturated sodium bicarbonate solution. Extraction with dichloromethane, followed by crystallization from ethyl acetate/n-hexane 2:1 gave 6.13 g (78%) N-benzyl-6-chloro-nicotinamide as light brown crystals of m.p.=113-114° C.

Aufarbeitung

  1. customThe solvent and excess thionyl chloride were removed under reduced pressure
  2. dissolutionthe residue was dissolved in 50 ml dichloromethane
  3. temperatureAfter cooling to 0° C.
  4. extractionExtraction with dichloromethane
  5. customfollowed by crystallization from ethyl acetate/n-hexane 2:1

Quellen und Nachweise

ORD-Eintrag
ord-ee0714062a624bb7af8d8ce0986a5eb3
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303790B1

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