Dichloromethane → 1-(2-chloro-4-iodo-phenyl)-5-methyl-1H-tetrazole

Temperatur

0 °C

A suspension of N-(2-chloro-4-iodo-phenyl)-acetamide (2.39 g, 8.09 mmol) in acetonitrile (40 mL) at 25° C. was treated with methylene chloride (5 mL) to obtain a clear solution. The resulting solution was then treated with sodium azide (1.05 g, 16.18 mmol), and the reaction mixture was cooled to 0° C. The reaction mixture was then treated with trifluoromethanesulfonic anhydride (3.42 g, 12.13 mmol), and the resulting reaction mixture was allowed to warm to 25° C. where it was stirred overnight. The reaction mixture was then concentrated in vacuo. The residue was diluted with ethyl acetate (50 mL) and water (50 mL), and the two layers were separated. The aqueous layer was further extracted with ethyl acetate (1×30 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 hexanes/ethyl acetate) afforded 1-(2-chloro-4-iodo-phenyl)-5-methyl-1H-tetrazole (1.53 g, 59%) as a white solid: mp 128-130.5° C.; EI-HRMS m/e calcd for C8H6ClIN4 (M+) 319.9327, found 319.9325.

1. customto obtain a clear solution
2. customthe resulting reaction mixture
3. temperatureto warm to 25° C. where it
4. concentrationThe reaction mixture was then concentrated in vacuo
5. additionThe residue was diluted with ethyl acetate (50 mL) and water (50 mL)
6. customthe two layers were separated
7. extractionThe aqueous layer was further extracted with ethyl acetate (1×30 mL)
8. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×100 mL)
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD-Eintrag

ord-ada6ce2724774f7895f348e4d4a0a83a

Quelldatensatz

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06369232B1