| 3-( P -hydroxy-ethyl-sulfonyl)-N-ethyl aniline and 4-( 13 -hydroxy- ethyl-sulfonyl)-N-ethyl aniline are important intermediate for bifunctional reactive dyes. An ethyl group introduced on the bridge nitrogen atom of the MCT/VS bifunctional dye possesses higher reactivity, good permeability and buid-up properties and better fastness to chlorine bleach than that of imino bridge (no ethyl) dyes. Reductive alkylation of 3-( 13 -hydroxy-ethyl-sulfonyl) aniline with acetaldehyde and hydrogen in the presence of Raney nickel, more than 98% conversion and 94.5% selectivity of mono-alkylation were achieved. To prepare 3-( P -hydroxy-ethyl-sulfonyl)-N-ethylaniline from 3-( P - hydroxy-ethyl-sulfonyl)-nitrobenzene with hydrogen and acetaldehyde in the presence of Raney nickel by one pot-two steps method, 98%conversion ratio and 97.5% selectivity of 3-( 13 -hydroxy-ethyl- sulfonyl)-N-ethylaniline was given. Synthesizing 4-( P -hydroxy-ethyl-sulfonyl)-N-ethylaniline from 4-( 13 - hydroxy-ethyl-sulfonyl)-acetyl-aniline via hydrolysis and reductive alkylation, the yield of 4-( 13 -hydroxy-ethyl-sulfonyl)-aniline was 90-94%; the conversion and selectivity of reductive alkylation were 95% and 97% respectively. The single crystals of two Model compounds, 2,4-dimethoxy-6-anilino- triazine and 2,4-dimethoxy-6-(N-methyl-anilino)-triazine were obtained. Which were determined on CD-4 X-ray Deflector. The data indicated that the planar angle of triazine and phenyl ring of 2,4-dimethoxy-6-(N- methyl-anilino)-triazine was 72.220, and corresponding angle on model compound 2,4-dimethoxy-6-anilino-triazine was 90?It means that, due to steric hindrance, the co-planarity between above rings of the compound / ABSTRACT - III containing N-alkyl -imino-bridge was destroyed. Thus, the electrons transition from the alone pair electrons on nitrogen atom to triazine ring would partly be prevented, the reactivity of N-alkylimino would be greater than the coiresponding N-imino compound. |
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