Thionyl Chloride → 5-(chloromethyl)-N-(3,4-dichlorobenzyl)pyridin-2-amine

Reaktionsgleichung

S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:9][NH:10][C:11]1[N:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][CH:12]=1>C(Cl)Cl>[Cl:3][CH2:17][C:14]1[CH:13]=[CH:12][C:11]([NH:10][CH2:9][C:8]2[CH:19]=[CH:20][C:21]([Cl:22])=[C:6]([Cl:5])[CH:7]=2)=[N:16][CH:15]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Thionyl chloride (0.103 mL, 1.413 mmol) was added to a suspension of (6-((3,4-dichlorobenzyl)amino)pyridin-3-yl)methanol (0.1 g, 0.353 mmol) in DCM (3.5 mL) cooled to 0° C. The mixture was stirred for 18 h at room temperature. The resulting white suspension was concentrated to yield 5-(chloromethyl)-N-(3,4-dichlorobenzyl)pyridin-2-amine, used in the next step without purification. 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.05 (1H, dd, J=9.29, 2.01 Hz), 7.92-8.01 (1H, m), 7.54-7.65 (2H, m), 7.36 (1H, dt, J=8.28, 1.00 Hz), 7.04-7.23 (1H, m), 4.65 (1H, s), 4.61 (2H, d, J=2.76 Hz), 4.39 (1H, s). LCMS: R.T.=2.96; [M+H]+=301.02.

Aufarbeitung

concentrationThe resulting white suspension was concentrated

Quellen und Nachweise

ORD-Eintrag: ord-ca4edfa26ac34f168ffb879199adac29
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08841301B2

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