Thionyl Chloride → 2-Chloromethyl-3-triphenylmethylthiopyridine hydrochloride

HRID 2085992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085992
O[CH2:2][C:3]1[C:8]([S:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:31])=O>CN(C)C=O>[ClH:31].[Cl:31][CH2:2][C:3]1[C:8]([S:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 99080472-Hydroxymethyl-3-triphenylmethylthiopyridine

Produkt 1

HCID 98459692-Chloromethyl-3-triphenylmethylthiopyridine hydrochlorideAusbeute 111,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
2 °C

Versuchsvorschrift

A thick suspension of 2-hydroxymethyl-3-triphenylmethylthiopyridine (90.3 g, 235 mmol) in N,N-dimethylformamide (270 mL) in a flask equipped with efficient mechanical stirring was chilled to 2° C. Thionyl chloride (25.8 mL, 354 mmol) was added in 5 mL portions over the period of 1 h while maintaining a temperature below 10° C. After completing the addition the reaction mixture was allowed to reach room temperature and was stirred for 30 min. The precipitate was filtered, washed with ethyl acetate (500 mL) and dried to give 86.7 g (84%) 2-chloromethyl-3-triphenylmethylthiopyridine hydrochloride as colorless crystals.

Aufarbeitung

  1. customequipped with efficient
  2. temperaturewhile maintaining a temperature below 10° C
  3. additionthe addition the reaction mixture
  4. customto reach room temperature
  5. stirringwas stirred for 30 min
  6. filtrationThe precipitate was filtered
  7. washwashed with ethyl acetate (500 mL)
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ed4386c655034ee58cd48866a7e3d073
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06723716B1

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