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

HRID 250091Notes

Reaction equation

HRID 250091 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

4

Reactant 2

HCID 3181862-Amino-5-chloro-4-methylpyridineHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridone

Product 1

HCID 574765835-Chloro-2-isothiocyanato-4-methylpyridineYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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, 1 H), 7.47 (s, 1 H), 2.37 (s, 3 H). LC/MS RT=2.79; [M+H]+=184.9.

Workup

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

Sources & evidence

ORD record
ord-71575eb5d31740fcbbf09e6f60a4c105
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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