Trimethyl orthoformate → 1-((4-methoxyphenyl)methyl)-1H-1,2,3,4-tetrazole

HRID 842755Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH3:11]OC(OC)OC.[N-:18]=[N+:19]=[N-:20].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:8]2[CH:11]=[N:20][N:19]=[N:18]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of 4-methoxybenzylamine (27 g), trimethylorthoformate (52.4 ml), sodium azide (19.2 g) and acetic acid (176 ml) was stirred at 80° C. for 14 h. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water and extracted with ethyl acetate. The extract was washed with a 1 N aqueous solution of hydrochloric acid, water, a saturated aqueous solution of sodium hydrocarbonate and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give the title compound (17.6 g) having the following physical data.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
dissolutionthe residue was dissolved in water
extractionextracted with ethyl acetate
washThe extract was washed with a 1 N aqueous solution of hydrochloric acid, water
dry with materiala saturated aqueous solution of sodium hydrocarbonate and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-ae55c629348c466aaa8022e2ef0c899c
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376484B1

Reaction notes

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