Methyl nitrite → HCID 57325265, compound

Participants

Reaction Conditions

Reaction Steps

In general analogy to the process described under 3.1, 59 g (0.48 mol) of thiophene-3-acetonitril are placed in a sulfonation flask and are charged with 19.2 g (0.48 mol) of sodium hydroxide, dissolved in 200 ml of methanol. 0.48 mol of gaseous methyl nitrite is introduced, with stirring, into this solution at 0-5° C. over 4.5 hours. The ice bath is then removed and the brown solution is stirred overnight at room temperature. The methanol is distilled off on a rotary evaporator and the resulting orange residue is charged with water and ethyl acetate. The aqueous phase is separated, washed twice with ethyl acetate and acidified with conc. HCl. The aqueous phase is extracted twice with ethyl acetate, the extracts are washed with water and dried over magnesium sulfate. After fitration, the solvent is distilled off and a brown solid is obtained which is then recrystallised from toluene, giving 28.6 g (39% of theory) of α-hydroxyiminothiophene-3-acetonitrile as a beige solid having a melting point of 96-106° C. The 1H-NMR spectrum is consistent with the proposed structure.

Provenance & Evidence