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

Temperature

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. This reaction mixture was added to 4.6 g of sodium azide (71 mmol) in 1.1 g (14 mmol) of pyridine 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. The crude product was recrystallized from 20 ml of isopropanol, giving 8.83 g of 1-methyl-5-benzoyltetrazole (purity 99.6%).

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 was recrystallized from 20 ml of isopropanol

ORD record

ord-e367809a15df44d488c35606de51a174

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536211B2