Thionyl Chloride → 2-Chloromethyl-3-triphenylmethylthiopyridine hydrochloride

HRID 2085992

Reaktionsgleichung

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

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

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

Quellen und Nachweise

ORD-Eintrag: ord-ed4386c655034ee58cd48866a7e3d073
Quelldatensatz: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06723716B1

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