Patent GB-1331606-A (GB)
Title: 4,5,6,7-tetrahydrobenzotriazoles
IPC: C23F11/14
Filed: 1970-09-25
Abstract: 1331606 Tetrahydrobenzotriazoles RHEINCHEMIE RHEINAU GmbH 25 Sept 1970 [26 Sept 1969] 45687/70 Heading C2C [Also in Division C5] Tetrahydrobenzotriazoles of Formulae Ia and Ib in which R 1  is a hydrogen atom, an unbranched or a branched alkyl radical having 1 to 18 carbon atoms, a 5- or 6-ring-membered cycloalkyl, alkylcycloalkyl or cycloalkyl-alkyl radical having 1 to 18 carbon atoms in the alkyl radical, a glucosyl, arabinosyl, xylosyl, ribosyl or another sugar radical derived from hexoses, pentoses or tetroses, or when R 2  and R 3  are H, a methoxycarbonylethyl radical or, alternatively, R 1  represents the radical A-Z in which A is an unbranched or branched alkylene radical having 1 to 4 carbon atoms and Z is an amino, lower monoalkylamino, di-(lower alkyl) amino, morpholino, pyrrolidino, piperidino, piperazino, N<SP>1</SP>- lower - alkyl - piperazino, N<SP>1</SP> - (# - hydroxylower alkyl) - piperazino or N<SP>1</SP> - (# - hydroxyalkoxy - lower - alkyl) - piperazino group, or R 1  represents a hydroxyalkyl or a carboxyalkyl group having 1 to 4 carbon atoms in the alkyl radical, a dialkylamino-ethylamino-carbonyl-alkyl or dialkylaminoethoxycarbonylalkyl group having 1 to 4 carbon atoms in the alkyl radicals, a carboxycyclohexyl radical, a phenyl, alkylphenyl or an alkoxyphenyl radical having 1 or 2 carbon atoms in the alkyl or alkoxy radical, a fluoro-, trifluoromethyl- or a carboxy-phenyl radical, a phenylalkyl radical having 1 to 4 carbon atoms in the alkyl radical, a fluorophenylalkyl, carboxy-phenylalkyl or an acylaminophenylalkyl radical having 1 to 8 carbon atoms in the acyl radical, an imidazolylalkyl, triazolylalkyl, or tetrazolylalkyl radical having 1 to 4 carbon atoms in the alkyl radical, R 2  is a hydrogen atom, an unbranched or branched alkyl radical having 1 to 18 carbon atoms, a cyclohexyl or phenyl radical, a carboxyl group or an alkoxycarbonyl radical having 1 to 4 carbon atoms in the alkoxy radical, and R 3  is a hydrogen atom or an unbranched or branched alkyl radical having 1 to 4 carbon atoms, which are novel except for 4,5,6,7-tetrahydrobenzotriazole, 1 - phenyl - 4,5,6,7 - tetrahydrobenzotriazole and 1 - phenyl - 5 - methyl- 4,5,6,7 - tetrahydrobenzotriazole, are prepared by hydrogenating in the form of an acid addition salt which may be formed in situ from the free base and at least, one equivalent per basic group of an acid which forms a salt with the benzotriazole and in the presence of a palladium, platinum or rhodium catalyst, and at a temperature and pressure at which hydrogenation takes place, a benzotriazole of the formula IIa or IIb the reaction taking place in solution or a diluent in which the benzotriazole salt is at least partly soluble, and, if necessary, converting the resulting salt of the 4,5,6,7-tretrahydrobenzotriazole into another acid addition salt, a quaternary ammonium salt or the free base. In examples, 4,5,6,7-tetrahydrobenzotriazole, and 5-carboxy-, 1-ethyl-, 2-ethyl-, 1-hexadecyl- 1 - (2 - carboxyethyl)-, 1 - (2 - methoxycarbonylethyl)-, 1 - [1 - carboxypropyl - (2)]-, 1 - phenyl-, 1 - cyclohexyl-, 1 - cyclohexylmethyl-, 1 - (4 - acetamidobenzyl)-, 5 - methyl-, 5 - carboxy-, 4,6 - dimethyl-, 5,6 - dimethyl- and 1 - hexadecyl - 5 - methoxycarbonyl- 4,5,6,7-tetrahydrobenzotriazoles are prepared.