3,5-Dichloro-3-pyridylamine → 3,5-Dichloro-2-isothiocyanatopyridine

HRID 250103

Reaction equation

HRID 250103 reaction equation
[Cl:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:10](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:11]>ClCCl>[Cl:1][C:2]1[C:3]([N:9]=[C:10]=[S:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 778863,5-Dichloro-3-pyridylamineHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridone

Product 1

HCID 233404453,5-Dichloro-2-isothiocyanatopyridineYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To 3,5-dichloropyridin-2-amine (0.36 g, 2.209 mmol) in dichloromethane (25 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.523 g, 2.253 mmol). The reaction was stirred at 40° C. for 3 hours. The reaction was cooled to room temperature and the crude was purified by chromatography (Biotage: 25-100% ethyl acetate/hexane) to yield to yield 3,5-dichloro-2-isothiocyanatopyridine (0.4 g, 1.951 mmol, 88% yield). 1H NMR (500 MHz, DMSO-D6) δ ppm 8.50 (t, J=2.59 Hz, 1 H), 8.45 (t, J=2.59 Hz, 1 H). MS (LC/MS) R.T.=2.07; [M+H]+=204.8.

Workup

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

Sources & evidence

ORD record
ord-3c18546b68874bb7ba4a02a5fef5411a
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Linked notes

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