反应详情

To 0.017 mole of sodium hydride, obtained from 0.82 g. of a 50% dispersion of sodium hydride in mineral oil, was added 50 ml. of dimethylformamide. To the mixture there was added 5.0 g. (0.018 mole) of 2,6-dinitro-N-methoxy-α,α,α-trifluoro-p-toluidine (Example 5), and the mixture was heated for about 45 minutes at temperatures up to about 65° C. The reaction mixture was then cooled to room temperature and there was added thereto, dropwise, 5.3 g. (0.034 mole) of ethyl iodide. The mixture was allowed to stir at room temperature for about 30 minutes and was then heated for about 1 hour at about 80° C., and was checked by TLC. No starting material appeared on the thin layer chromatogram. The reaction product mixture was cooled and allowed to stand overnight at ambient room temperature. The reaction product mixture was worked up by diluting it with ether and washing several times with dilute aqueous hydrochloric acid, once with water, and drying the organic phase over anhydrous magnesium sulfate. The drying agent was filtered off and the solvent removed in vacuo. The residue was chromatographed on a Florisil column using benzene both as solvent and as eluent. The first fractions collected appeared to contain the desired product. The fractions were combined, the solvent was removed in vacuo, and the residue thus obtained was recrystallized from petroleum ether (b.p. 60°-71° C.). The product had a melting point of about 95°-97° C., weighed 1.0 g., and was identified by NMR spectrum and elemental analyses as 2,6-dinitro-N-ethyl-N-methoxy-α,α,α-trifluoro-p-toluidine.

1. additionTo the mixture there was added 5.0 g
2. additionthere was added
3. temperaturewas then heated for about 1 hour at about 80° C.
4. temperatureThe reaction product mixture was cooled
5. waitto stand overnight at ambient room temperature
6. washwashing several times with dilute aqueous hydrochloric acid
7. dry with materialonce with water, and drying the organic phase over anhydrous magnesium sulfate
8. filtrationThe drying agent was filtered off
9. customthe solvent removed in vacuo
10. customThe residue was chromatographed on a Florisil column
11. customThe first fractions collected
12. customthe solvent was removed in vacuo
13. customthe residue thus obtained
14. customwas recrystallized from petroleum ether (b.p. 60°-71° C.)