GB1189537A - One-Component Diazotype Material - Google Patents

Abstract

1,189,537. Diazonium compounds. KALLE A.G. 4 July, 1967 [6 July, 1966], No. 30768/67. Heading C2C. [Also in Division G2] Diazonium compounds of formula wherein R 1 is hydrogen, alkyl or alkaryl and R 2 is aoyl, sulphonyl, carboxyethyl or carbamyl or wherein R 6 completes a 6-membered heterocyclic ring with the nitrogen and carbon atoms or, R 1 and R 2 are R 7 -CO- where R 7 is a 5-membered heterocyclic ring with the carbon and nitrogen atoms, R 3 is alkyl, R 4 is alkyl or aralkyl or R 3 and R 4 together complete a 6-membered heterocyclic ring, R 5 is hydrogen, halogen, alkyl, alkoxy or alkyl- or aryl-mercapto and X is an anion, are prepared by one of the following methods: (1) where R 1 and R 5 are hydrogen.-1-chloro- 2,4-dinitrobenzene is reacted with the appropriate secondary amine or heterocyclic base to obtain the desired substituents R 3 and R 4 in the 1-position. The nitro group in the 2- position is now reduced with sodium polysulphide and the amino group thus formed is reacted with the appropriate carboxylic chloride or anhydride, alkyl or aryl sulphochloride or cyanuric chloride to obtain the desired R 2 group. If a 2-oxo-pyrrolidone ring is desired (cf Formula 27), this is obtained by reaction with butyrolactone with zinc chloride. The 4-nitro group is reduced and diazotized to produce the desired diazotized product. (2) where R 1 is alkyl.-This is as method (1) except after reduction of the nitro group in the 2-position, the compound is reacted with a monohaloalkyl compound before acylation. (3) where R 5 is halogen, alkoxy or alkyl.-1- chloro-2-nitro-5-halo-alkoxy or -alkyl benzene is reacted as in method (1) or (2) to produce the -NR 3 R 4 group in the 1-position and the -NR 1 R 2 group in the 2-position. The compound is then coupled with a diazonium compound in the 4-position and then reduced to leave a diazonium group in the 4-position or by introduction of a nitro group in the 4-position followed by reduction and diazotization. (4) wherein R is alkyl- or aryl-mercapto.-1,5- dichloro-2-nitro-benzene is reacted as in method (1) or (2) to obtain a -NR 3 R 4 group in the 1-position and a -NR 1 R 2 group in the 2- position. The compound is now nitrated to form a 4-nitro group and then the 5-chloro radical is replaced by an alkyl- or aryl-mercapto group. The 4-nitro group is then reduced and diazotized to produce the diazonium compound.