1,1'-Thiocarbonyldi-2(1H)-pyridone → 6,8-Dichloro-3-isothiocyanatoisoquinoline

HRID 250116Notes

Reaction equation

HRID 250116 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH:8]=[N:7][C:6]([NH2:13])=[CH:5]2.[C:14](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:15]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH:8]=[N:7][C:6]([N:13]=[C:14]=[S:15])=[CH:5]2

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 534044276,8-Dichloroisoquinolin-3-amine

Product 1

HCID 574765996,8-Dichloro-3-isothiocyanatoisoquinolineYield 61.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To 6,8-dichloroisoquinolin-3-amine (0.27 g, 1.28 mmol) in dichloromethane (20 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (0.30 g, 1.29 mmol) and the reaction mixture was stirred at 40° C. for 4 hours. The reaction was cooled to room temperature and chromatographed (Biotage: 10-100% ethyl acetate/hexanes) to yield 6,8-dichloro-3-isothiocyanatoisoquinoline (0.2 g, 0.78 mmol, 61.9% yield) as a powder. 1H NMR (500 MHz, DMSO-D6) δ ppm 9.42 (s, 1H), 8.16 (d, J=1.83 Hz, 1H), 8.02 (d, J=2.14 Hz, 1H), 7.92 (s, 1H). MS (LC/MS) R.T.=3.63; [M+H]+=255.0.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customchromatographed (Biotage: 10-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a2bd1a1e22a84a60afe451d98821ef87
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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