2-Amino-5-chloro-4-methylpyridine → 5-Chloro-2-isothiocyanato-4-methylpyridine

HRID 1875956Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:10](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:11]>ClCCl>[Cl:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([N:8]=[C:10]=[S:11])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To 5-chloro-4-methylpyridin-2-amine (0.41 g, 2.88 mmol) in dichloromethane (25 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.70 g, 3.0 mmol). The reaction was stirred at 40° C. for 3 hours. The reaction was cooled to room temperature. The crude mixture was purified by chromatography (Biotage: 25-100% ethyl acetate/hexane) to yield 5-chloro-2-isothiocyanato-4-methylpyridine (0.45 g, 2.44 mmol, 85% yield). 1H NMR (500 MHz, DMSO-D6) δ ppm 8.45 (s, 1H), 7.47 (s, 1H), 2.37 (s, 3H). LC/MS RT=2.79; [M+H]+=184.9.

Workup

temperatureThe reaction was cooled to room temperature
customThe crude mixture was purified by chromatography (Biotage: 25-100% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-0c2c864ff82e4d59b589e9dbd9167470
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309577B2

Reaction notes

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