1,1'-Thiocarbonyldi-2(1H)-pyridone → 4,5-Dichloro-2-isothiocyanatopyridine

HRID 250089

Reaction equation

HRID 250089 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([NH2:9])[CH:3]=1.[C:10](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:11]>ClCCl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([N:9]=[C:10]=[S:11])[CH:3]=1

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 107733044,5-Dichloropyridin-2-amine

Product 1

HCID 574765824,5-Dichloro-2-isothiocyanatopyridineYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To 4,5-dichloropyridin-2-amine (0.25 g, 1.53 mmol) in dichloromethane (25 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.36 g, 1.56 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) to yield 4,5-dichloro-2-isothiocyanatopyridine (0.26 g, 1.27 mmol, 83% yield) as a yellow powder. The product was carried directly to the next step.

Workup

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

Sources & evidence

ORD record
ord-961709d812154abfa757a2520f1a898e
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Linked notes

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