Water → 5-Bromo-2-(5-methyl-tetrazol-1-yl)-phenylamine

Temperatur

25 °C

A suspension of 1-(4-bromo-2-nitro-phenyl)-5-methyl-1H-tetrazole (1.13 g, 3.98 mmol) in methanol (40 mL, not completely dissolved in methanol even at hot conditions) was treated sequentially with ammonium chloride (3.19 g, 59.7 mmol), zinc dust (2.60 g, 39.8 mmol), and water (20 mL). Initially after the addition, the reaction was exothermic. The reaction mixture was then stirred for 1 h at 25° C. The reaction mixture was then filtered, and the residue was washed with methanol (50 mL) and ethyl acetate (100 mL). The filtrate was concentrated in vacuo, and the organic compound was extracted into ethyl acetate (3×50 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 5-bromo-2-(5-methyl-tetrazol-1-yl)-phenylamine (0.90 g, 97%) as a white solid: EI-HRMS m/e calcd for C8H8BrN5 (M+) 252.9963, found 252.9962.

1. additionInitially after the addition
2. filtrationThe reaction mixture was then filtered
3. washthe residue was washed with methanol (50 mL) and ethyl acetate (100 mL)
4. concentrationThe filtrate was concentrated in vacuo
5. extractionthe organic compound was extracted into ethyl acetate (3×50 mL)
6. washThe combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×200 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD-Eintrag

ord-9227cc1d6bec4d48be4d0f3f80761a06

Quelldatensatz

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06441180B1