1,1'-Thiocarbonyldi-2(1H)-pyridone → 2,3-Dichloro-6-isothiocyanatopyridine

HRID 1875952Notes

Reaction equation

HRID 1875952 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[N:6][C:7]=1[Cl:8].[C:10](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:11]>ClCCl.C(OCC)(=O)C.CCCCCC>[Cl:8][C:7]1[C:2]([Cl:1])=[CH:3][CH:4]=[C:5]([N:9]=[C:10]=[S:11])[N:6]=1

Participants

5

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 534855065,6-Dichloropyridin-2-amine

Product 1

HCID 574765812,3-Dichloro-6-isothiocyanatopyridineYield 81.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
40 °C

Procedure

To 5,6-dichloropyridin-2-amine (0.47 g, 2.88 mmol) in dichloromethane (25 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.68 g, 2.94 mmol). The reaction was stirred at 40° C. for 3 hours, then cooled to room temperature. The crude material was purified by chromatography (Biotage: 25-100% ethyl acetate/hexane) 2,3-dichloro-6-isothiocyanatopyridine (0.48 g, 2.34 mmol, 81% yield) as a white powder. 1H NMR (500 MHz, DMSO-D6) δ ppm 8.26 (d, J=8.55 Hz, 1H), 7.47 (d, J=8.24 Hz, 1H). MS (LC/MS) R.T.=2.83; [M+H]+=204.8.

Workup

  1. temperaturecooled to room temperature

Sources & evidence

ORD record
ord-a645c828ec1e4eec9da2115c957d7a4c
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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