反应详情

Magnesium (0.3 g) is suspended in dried tetrahydrofuran (5 ml). To the suspension is added a small piece of iodine with stirring in nitrogen gas flow, and further added 1-methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazole (0.3 g). To the mixture is added ethyl bromide (0.1 ml), and the reaction is started by heating the mixture from outside. A solution of 1-methyl-5-(3-chloropropyl)thio-1,2,3,4-tetrazole (1.8 g) in dried tetrahydrofuran (15 ml) is additionally added dropwise to the mixture. After the solution is added, the mixture is refluxed for 1 hour. To the obtained Grignard reagent is added dropwise a solution of propionitrile (0.5 g) in dried tetrahydrofuran (5 ml) with stirring under ice-cooling, and the mixture is stirred for 3 hours at room temperature. To the mixture is added 1 N-HCl (20 ml) under ice-cooling and the mixture is stirred for 1 hour. The reaction mixture is diluted with water and extracted with chloroform. The chloroform solution is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride and dried over sodium sulfate. After chloroform is distilled off, the residue is purified by silica gel column chromatography (Kieselgel 60) and eluted with benzene-ether (10:1) to give 1-methyl-5-(3-propionylpropyl)thio-1,2,3,4-tetrazole (0.5 g) as colorless liquid, nD25 =1.5042.

1. temperatureby heating the mixture from outside
2. additionAfter the solution is added
3. temperaturethe mixture is refluxed for 1 hour
4. temperaturecooling
5. stirringthe mixture is stirred for 3 hours at room temperature
6. temperaturecooling
7. stirringthe mixture is stirred for 1 hour
8. extractionextracted with chloroform
9. washThe chloroform solution is washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
10. dry with materialdried over sodium sulfate
11. distillationAfter chloroform is distilled off
12. customthe residue is purified by silica gel column chromatography (Kieselgel 60)
13. washeluted with benzene-ether (10:1)