The Chemistry of Synthetic Dyes by K Venkataraman (Eds.)

By K Venkataraman (Eds.)

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D. TIL AK 26 CONH—A—CONH—B (LXI) A = Substituted or unsubstituted arylene with hal, alk, O-Alk, O-Ar, or halogenated aryloxy groups. B = Ph, a-naphthyl, or jS-naphthyl substituted with hal, alk, O-Alk, CF 3 , CN, R-CO, Ar-CO, N 0 2 , CONH-Alk, S0 2 NH-Alk, S0 2 -Alk, S0 2 -Ar Y and Z = H or one is alkyl Cl + / COC1 \^-CONH—/ NH2 \—Cl Cl (LXII) Cl CONH—/ CONH—f (LXIII) \ \—Cl Cl ODCB Reflux 6hr 27 I. NAPHTHOQUINONOID DYES AND PIGMENTS + H2N—/ \ COOH COC1 ODCB 6hr SOCI2 CONH—K (LXIV) r\ CONH—// V-COC1 (LXV) r\ CONH—f Cl V-CONH—f V-Cl Cl (LXVI) CONH—^ ^t—NHCO N ^ ^ (LXVII) \—COOH 28 B.

NAPHTHOQUINONOID DYES AND PIGMENTS 25 weak shades and therefore are of no interest as vat dyes. 40 To prepare useful vat dyes, l-carbethoxy-2,3-phthaloylpyrrocoline was hydrolyzed by alcoholic alkali to the 1-carboxy derivative, which was then converted to the 1-carbonyl chloride. 41* 42 These arylides, with the exception of those derived from benzidine and o-tolidine (LIX), are only weakly substantive to cotton. The dyes of type (LIX) dyed attractive fast violet shades on cotton. 42 An interesting dye obtained in this work is (LX) from (I) and Naphtol AS-LG and ASL3G.

A tentative mechanism of formation of the latter from (CII) is indicated. 67 J. N. ) Thesis, University of Bombay (1969). I. NAPHTHOQUINONOID DYES AND PIGMENTS CHART 11 + (A) CH2CI2 ^-i> 41 42 B. D. TIL AK The third route, developed by Shah and Tilak, 67 for the synthesis of (C) is outlined in Chart 12. The compounds (CI), (CII), (CIII) on heating to their melting points or on sublimation yield 2,3-phthaloylpyrrocoline (XXXVII) (yield + (XXXVII) (< 1%) (C 6 H 5 ) 3 CH + (Cl) (6%) + (29%) 10-15%) with the elimination of 2-mercaptomethylpyridine (identified as the disulfide), HC1 and sulfur, and hydrogen sulfide, respectively.

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