Thionyl Chloride → 8-(Chloromethyl)-2-methylimidazo[1,2-a]pyridine

HRID 544475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544475
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([CH2:10]O)=[CH:8][CH:7]=[CH:6][N:5]2[CH:12]=1.S(Cl)([Cl:15])=O>ClCCl>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([CH2:10][Cl:15])=[CH:8][CH:7]=[CH:6][N:5]2[CH:12]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 139003302-Methylimidazo[1,2-a]pyridine-8-methanol

Produkt 1

HCID 139003318-(Chloromethyl)-2-methylimidazo[1,2-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Methyl-8-hydroxymethylimidazo[1,2-a]pyridine 21.4 g (0.13 mol) is dissolved in 400 ml dichloromethane. To the solution at 0° C. is added dropwise with stirring 19 ml of thionyl chloride. The reaction mixture is stirred for one hour and the dichloromethane is removed under reduced pressure. The residue is dissolved in distilled water, neutralizedat 0° C. with ammonium hydroxide and extracted with dichloromethane.The extracts are combined and dried over anhydrous sodium sulfate. Following filtration, the dichloromethane is removed under reduced pressure to give 2-methyl-8-chloromethylimidazo[1,2-a]pyridine, mp. 110°-112° C.

Aufarbeitung

  1. additionTo the solution at 0° C. is added dropwise
  2. customthe dichloromethane is removed under reduced pressure
  3. dissolutionThe residue is dissolved in distilled water, neutralizedat 0° C. with ammonium hydroxide
  4. extractionextracted with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltration
  7. customthe dichloromethane is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7731897781ef4f7891f1857e8d858771
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04450164

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