Phenyl thioxochloroformate → 4-[1-(2,3-dichlorophenyl)ethyl]-1,3-dihydroimidazole-2-thione

A 1:1 mixture of 4-[1-(2,3-dichloro-phenyl)-ethyl]-1H-imidazole (Intermediate A4), and 4-[1-(2,3-dichloro-phenyl)-vinyl]-1H-imidazole (Intermediate A3) (0.77 g, 3.2 mmol) in tetrahydrofuran (THF) (10 mL) and water (10 mL) was treated with NaHCO3 (1.64 g, 19.5 mmol) at rt for 10 m. Phenyl chlorothionoformate (1.1 mL, 7.95 mmol) was added and stirring was continued for 5 h. The mixture was diluted with water and extracted with hexane:ethyl acetate (3×). The organic portions were combined, dried over MgSO4, filtered and the solvent was removed under vacuum. The residue was dissolved in MeOH (20 mL) and treated with triethylamine (NEt3) (1 mL) for 18 h at rt. The mixture was concentrated onto silica gel. The material was purified by elution from silica gel with 1 to 2% MeOH: CH2Cl2. The solids were titurated with CHCl3: hexanes and collected on a glass frit to give a white solid 4-[1-(2,3-dichloro-phenyl)-ethyl]-1,3-dihydro-imidazole-2-thione (Compound 1) 40 mg.

1. extractionextracted with hexane
2. dry with materialdried over MgSO4
3. filtrationfiltered
4. customthe solvent was removed under vacuum
5. dissolutionThe residue was dissolved in MeOH (20 mL)
6. additiontreated with triethylamine (NEt3) (1 mL) for 18 h at rt
7. concentrationThe mixture was concentrated onto silica gel
8. customThe material was purified by elution from silica gel with 1 to 2% MeOH
9. customhexanes and collected on a glass frit

ORD record

ord-8be801dd1b834abda28772732c215a44

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683089B1