Reaktion #1161373

Reaktionsgleichung

1-fluoro-2-nitrobenzene

2-mercapto-1-methylimidazole

sodium hydride

sodium chloride

hydrogen

→

product

Ausbeute 74.4%

1-Methyl-2-[(2-nitrophenyl)thio]-1H-imidazole

Ausbeute 74.4%

Lösungsmittel

N,N-dimethylformamide

N,N-dimethylformamide

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe ice bath was removed
2. 2
   workup.ADDITIONTo the reaction was added
3. 3
   workup.STIRRINGAfter stirring at room temperature for 16 hours
4. 4
   Extraktionextracted with dichloromethane
5. 5
   SonstigeThe organics were dried
6. 6
   Sonstigethe solvents were removed in vacuo
7. 7
   SonstigeThe resulting yellow solid was triturated with ether
8. 8
   Filtrationcollected by filtration

Vorschrift

To a slurry of 0.8 g (20 mmoles) of sodium hydride (60% dispersion in mineral oil) in 10 ml of N,N-dimethylformamide, stirred in an ice bath, and under a nitrogen atmosphere, was added dropwise a solution of 2.28 g (20 mmoles) of 2-mercapto-1-methylimidazole in 5 ml of N,N-dimethylformamide. After the evolution of hydrogen gas had ceased, the ice bath was removed and the reaction mixture stirred at room temperature for 0.5 hours. To the reaction was added, dropwise, a solution of 2.82 g (20 mmoles) of 1-fluoro-2-nitrobenzene in 10 ml of N,N-dimethylformamide. After stirring at room temperature for 16 hours, the mixture was poured into a saturated sodium chloride solution (100 ml) and extracted with dichloromethane. The organics were dried and the solvents were removed in vacuo. The resulting yellow solid was triturated with ether and collected by filtration to give 3.5 g (74%) of product as yellow prisms, mp 117°-119° C.

Quelle