Benzoyl chloride → (1-methyl-1H-tetrazol-5-yl)(phenyl)methanone

温度

60 °C

At room temperature, 10 g of benzoyl chloride (71 mmol) were admixed with 3.7 g (92 mmol) of methyl isocyanide. The mixture was then heated at 60° C. for 3 hours. The mixture was admixed with 25 ml of acetonitrile and cooled to 0° C. The reaction mixture was added to 4.6 g of sodium azide (71 mmol) in 9.1 g of 2,6-dimethylpyridine (85 mmol) in 25 ml of acetonitrile at 0° C. The mixture was then heated to 60° C. and stirred at this temperature for 1 hour. At room temperature, 100 ml of water and 100 ml of ethyl acetate were added to the mixture. The organic phase was separated off and the aqueous phase was extracted with 100 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and the solvent was removed in vacuo. This gave 1-methyl-5-benzoyltetrazole in a yield of 82% (purity 90%) based on the acid chloride used. The crude product could be recrystallized from 20 ml of isopropanol, giving 9.4 g of 1-methyl-5-benzoyltetrazole (purity 97.4%).

1. customAt room temperature
2. temperaturecooled to 0° C
3. temperatureThe mixture was then heated to 60° C.
4. customThe organic phase was separated off
5. extractionthe aqueous phase was extracted with 100 ml of ethyl acetate
6. dry with materialThe combined organic phases were dried over magnesium sulphate
7. customthe solvent was removed in vacuo
8. customThe crude product could be recrystallized from 20 ml of isopropanol

ORDレコード

ord-d8e9b8d51a144b619f7fb685b13a5a69

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08536211B2