Methyl isothiocyanate → 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-(N-methylthiocarbamoyl)oxymethyl-1H-imidazole

To a dry tetrahydrofuran-dimethylformamide (1:1 v/v, 1 ml)solution of 50 mg (0.15 mmol)of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]-methanol (Compound I-8)was added 6.6 mg (0.17 mmol)of 60% sodium hydride under nitrogen atomosphere, and the mixture was stirred at room temperature for 30 minutes. Then, 22 mg (0.3 mmol)of methylisothiocyanate was added under ice-cooling. The mixture was stirred at the same temperature for 30 minutes, and at room temperature for 30 minutes. To the reaction mixture, an aqueous ammonium chloride solution was added to terminate the reaction. The mixture was extracted with diethyl ether. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:1)to give 37 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-2-(N-methylthiocarbamoyl)oxymethyl-1H-imidazole (Compound I-44)(yield 60%). mp 119-121° C.

1. temperaturecooling
2. stirringThe mixture was stirred at the same temperature for 30 minutes
3. waitat room temperature for 30 minutes
4. customto terminate
5. customthe reaction
6. extractionThe mixture was extracted with diethyl ether
7. washThe organic layer was washed with saturated brine
8. dry with materialdried over magnesium sulfate
9. concentrationThe solvent was concentrated under reduced pressure
10. customthe residue was purified by silica gel chromatography (ethyl acetate

ORDレコード

ord-7122d943f605423393d78cf79858e066

出典データセット

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05910506