GB1199742A - Diazotype Material - Google Patents

Abstract

1,199,742. Diazonium compounds. VAN DER GRINTEN N.V. 15 Sept., 1967 [24 Sept., 1966], No. 42120/67. Addition to 919,037. Heading C2C. [Also in Division G2] Diazonium compounds of formula wherein X is an anion, R 1 is methyl, R 2 is ethoxy, R 3 and R 4 are unsubstituted or substituted alkyl, aralkyl or cycloalkyl or together complete a saturated heterocyclic ring and Z is hydrogen, halogen, methyl, alkoxy or dialkylamino are prepared by (1) reacting the appropriate 2 - chloro - 4 - (disubstituted amino) - 5 - phenoxy-nitrobenzene with methylamine to form the 2-methylamino compound, reacting with ethyl chloroformate to form the 2-(N-methyl- N-ethoxycarbonyl) compound and then reducing and diazotizing to produce the diazonium compound, (2) reacting 3-amino-4-phenoxy chlorobenzene with ethylene oxide to produce 3-(N,N<SP>1</SP>- bis-2-hydroxyethyl)-4-phenoxy chlorobenzene, nitrating the chlorobenzene and then reacting the concentrated compound as in (1) above to produce the diazonium compound, and (3) nitrating 3-amino-4-phenoxy chlorobenzene, reacting the product with methylamine and ethyl chloroformate as in (1) above to produce 2-(N- methyl - N - ethoxycarbonyl) amino - 4 - amino - 5 - phenoxy-nitrobenzene, diazotizing and performing a Sandmeyer reaction on the diazotized product to produce the 4-chloro compound. This is reacted with morpholine, reduced and diazotized in the 1-position to produce the diazonium compound. A similar compound in which R 2 is methyl is obtained when a cetyl chloride is employed instead of ethyl chloroformate.