1,1'-Thiocarbonyldi-2(1H)-pyridone → 2-(4-chloro-1H-imidazol-1-yl)-5-isothiocyanato-3-methoxypyridine

HRID 1803163Notes

Reaction equation

HRID 1803163 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[N:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=2[O:14][CH3:15])[CH:6]=1.[C:16](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:17]>ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[C:8]([O:14][CH3:15])=[CH:9][C:10]([N:13]=[C:16]=[S:17])=[CH:11][N:12]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 580754656-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-amine

Product 1

HCID 866499162-(4-chloro-1H-imidazol-1-yl)-5-isothiocyanato-3-methoxypyridineYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step O (3): Dichloromethane (100 mL) was added to a flask charged with 6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-amine (3.0 g, 13.35 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (3.10 g, 13.35 mmol). The resulting mixture was stirred for 18 h at rt. The reaction mixture was concentrated in vacuo. The crude products were purified using silica gel chromatography (0-5% EtOAc/chloroform, linear gradient) to afford 2-(4-chloro-1H-imidazol-1-yl)-5-isothiocyanato-3-methoxypyridine (2.89 g, 81% yield) as a yellow solid. LC-MS (M+H)+ 267.1. 1H NMR (500 MHz, chloroform-d) δ ppm 8.30 (s, 1 H) 8.02 (s, 1 H) 7.72 (s, 1 H) 7.20 (s, 1 H) 4.00 (s, 3 H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude products were purified

Sources & evidence

ORD record
ord-c67dc735cd6449988ab2f1b429d505c8
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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