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Isothiocyanates. III. The preparation of m- and p-isothiocyanato derivatives of dimethylaminoazobenzene

K. Antoš

Slovak Technical University, Bratislava

Abstract: cf. CA 53, 21735f. Synthesis of some new m- and p-isothiocyanato derivs. of dimethylaminoazobenzene was described. From nitroanilines or nitrotoluidines by a direct diazotization and by coupling with dimethylaniline, nitro compds. were prepd. which by redn. form the corresponding amino derivs. By a direct action of thiophosgene, isothiocyanates were formed. By detg. IR spectra it was shown that the isothiocyanato group has a wide absorption band in the area 2100 cm^-1 and a smaller max. in the area 1430 cm^-1 The following were prepd. (R = pMe₂NC₆H₄N₂)(m.p. given): m-O2NC6R, 172-3°; mH₂NC₆H₄R, 171-2°; m-SCNC₆H₄R, 106°; p-O2NC6H4R, 238-9°; p-O2NC6H4R, 191-2° p-SCNC6H4R, 171-2°; 3,4-Me(O₂N)C₆H₃R, 158-9°; 3,4-Me(H₂N)C₆H₃R, 217°; 3,4-Me(SCN)C₆H₃R, 162-3°; 4,3-Me(O₂N)C₆H₃R, 148-9°; 4,3-Me(H₂N)C₆H₃R, 225-6° 4,3-Me(SCN)C₆H₃R, 122°; 2,4-Me(O₂N)C₆H₃R, 167-8°; 2,4-Me(H₂N)C₆H₃R, 155-6°; 2,4-Me(SCN)C₆H₃R, 129°; 2,5-Me(O₂N)C₆H₃R, 170°; 2,5-Me(H₂N)C₆H₃R, 148-9°; 2,5-Me(SCN)C₆H₃R, 153-4°.

Full paper in Portable Document Format: 142a105.pdf (in Slovak)

Chemical Papers 14 (2) 105–118 (1960)