Reaktion #1161387

Reaktionsgleichung

4-chloro-3-nitroanisole

2-mercapto-1-methylimidazole

sodium hydride

N,N-dimethylformamide

→

product

Ausbeute 38.0%

2-[(4-Methoxy-2-nitrophenyl)thio]-1-methyl-1H-imidazole

Ausbeute 38.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated at 90°-100° C. for 4 hours
2. 2
   workup.ADDITIONwas added
3. 3
   Sonstigethe mixture was partitioned between dichloromethane and dilute sodium bicarbonate
4. 4
   EinengenThe organics were concentrated on a steam bath to a small volume
5. 5
   Sonstigethe residue was chromatographed on silica gel
6. 6
   workup.ADDITIONThe fractions containing the product
7. 7
   Einengenconcentrated

Vorschrift

To a mixture of 2-mercapto-1-methylimidazole (1.14 g, 10 mmoles), 0.6 of 60% sodium hydride in mineral oil and 20 ml of N,N-dimethylformamide was added 1.88 g (10 mmoles) of 4-chloro-3-nitroanisole. The mixture was stirred at room temperature for 0.5 hours and then heated at 90°-100° C. for 4 hours. After cooling in an icebath, 0.5 ml of acetic acid was added and the mixture was partitioned between dichloromethane and dilute sodium bicarbonate. The organics were concentrated on a steam bath to a small volume and the residue was chromatographed on silica gel using ethyl acetate as the eluent. The fractions containing the product were combined and concentrated to give 1.0 g (38%) of the product, mp 117°-120° C.).

Quelle