1,1'-Thiocarbonyldi-2(1H)-pyridone → HCID 86649904, compound

HRID 1803139Notes

Reaction equation

HRID 1803139 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[C:13]([F:14])=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=2[F:15])[CH:6]=1.FC1C=C(C=C(F)C=1N1C=CN=C1)N.[C:30](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:31]>ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[C:8]([F:15])=[CH:9][C:10]([N:11]=[C:30]=[S:31])=[CH:12][C:13]=2[F:14])[CH:6]=1

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 86649905HCID 86649905, compound

Product 1

HCID 86649904HCID 86649904, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step J (3): Dichloromethane (15 mL) was added to a flask charged with a 1:1 mixture of 4-(4-chloro-1H-imidazol-1-yl)-3,5-difluoroaniline/3,5-difluoro-4-(1H-imidazol-1-yl)aniline (1.0 g, 4.36 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (1.012 g, 4.36 mmol). The resulting mixture was stirred for 16 h at rt. The crude reaction mixture was concentrated and the crude products were purified using silica gel chromatography (60% EtOAc/hexanes) to afford 4-chloro-1-(2,6-difluoro-4-isothiocyanatophenyl)-1H-imidazole (195 mg, 0.718 mmol, 17% yield). LC-MS (M+H)+ 272.0. 1H NMR (500 MHz, chloroform-d) δ ppm 7.57 (d, J=1.83 Hz, 1 H) 7.07 (d, J=1.53 Hz, 1 H) 6.94-7.04 (m, 2 H).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. customthe crude products were purified

Sources & evidence

ORD record
ord-3656e9d62891424999f18f0370db87a3
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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