Thionyl Chloride → 2-Chloromethyl-4-dimethylaminomethylpyridine dihydrochloride

HRID 851487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851487
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11]O)[CH:6]=1)[CH3:3].S(Cl)([Cl:15])=O>ClCCl>[ClH:15].[ClH:15].[Cl:15][CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH:10]=[CH:9][N:8]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 132926014-Dimethylaminomethyl-2-hydroxymethylpyridine

Produkt 1

HCID 132926032-Chloromethyl-4-dimethylaminomethylpyridine dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4-Dimethylaminomethyl-2-hydroxymethylpyridine (13.45 g) in dichloromethane (200 ml) was added dropwise to a stirred solution of thionyl chloride (30 ml) in dichloromethane (150 ml). The resulting red mixture was stirred for 1 hour then concentrated in vacuo. The residue was treated with ether (300 ml) to yield a crystalline solid. Recrystallisation from methanol/ether (1:3) yielded 2-chloromethyl-4-dimethylaminomethylpyridine dihydrochloride (20.04 g) as an orange solid m.p. 202°-204°.

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was treated with ether (300 ml)
  3. customto yield a crystalline solid
  4. customRecrystallisation from methanol/ether (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-f44ed5193f964f1d8a59463af90e2a6b
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04385058

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