Triethylamine → 2,4-Dichloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl]-3-pyridinecarboxamide

HRID 1791101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791101
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=O.Cl.[NH2:13][CH2:14][C:15]1[C:20]([Cl:21])=[CH:19][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:17][N:16]=1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:4]([NH:13][CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:17][N:16]=2)=[O:6])=[C:7]([Cl:11])[CH:8]=[CH:9][N:10]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 105838872,4-Dichloronicotinic AcidHCID 114997441-[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]methanamine hydrochloride

Produkt 1

HCID 220273562,4-Dichloro-N-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl]-3-pyridinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A solution of 0.22 g of the acid from Step C was refluxed in thionyl chloride for 1 hour followed by removal of the solvent under vacuum to give an oil. The oil was dissolved in 1 mL of methylene chloride and added to a solution of 2-aminomethyl-3-chloro-5-trifluoromethylpyridine hydrochloride (0.25 g) and triethylamine (0.20 g) in 9 mL of methylene chloride at room temperature. The reaction mixture was stirred at room temperature overnight. The reaction mixture was then filtered through silica gel, eluting with 100% methylene chloride. Removal of the solvent under vacuum provided the title compound as a solid, m.p. 122-124° C.

Aufarbeitung

  1. customfollowed by removal of the solvent under vacuum
  2. customto give an oil
  3. filtrationThe reaction mixture was then filtered through silica gel
  4. washeluting with 100% methylene chloride
  5. customRemoval of the solvent under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8ee93a0b463c4dbb86a4cad82feafe87
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074742B2

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