Patent ID: 6353113
Filing Date: 2002-03-05
Classification: C07C,C07D

Abstract:
A process for preparing a compound of formula I whereinG1 is hydrogen or chloro, G2 is perfluoroalkyl of 1 to 12 carbon atoms, E1 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by one to three alkyl of 1to 4 carbon atoms; or E1 is alkyl of 1 to 24 carbon atoms substituted by one or two hydroxy groups, E2 is straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by one to three alkyl of 1to 4 carbon atoms; or E2 is said alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more â€”OH, â€”OCOE11, â€”OE4, â€”NCO, â€”NHCOE11 or â€”NE7E8, or mixtures thereof, where E4 is straight or branched chain alkyl of 1to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms; or said alkyl or said alkenyl interrupted by one or more â€”Oâ€”, â€”NHâ€”or â€”NE4â€” groups or mixtures thereof and which can be unsubstituted or substituted by one or more â€”OH, â€”OE4 or â€”NH2 groups or mixtures thereof; or E2 is â€”(CH2)mâ€”COâ€”E5; E5 is OE6 or NE7E8, or E5 is â€”PO(OE12)2, â€”OSi(E11)3 or â€”OCOâ€”E11, or straight or branched chain C1-C24alkyl which can be interrupted by â€”Oâ€”, â€”Sâ€”or â€”NE11 and which can be unsubstituted or substituted by â€”OH or â€”OCOâ€”E11, C5-C12 cycloalkyl which is unsubstituted or substituted by â€”OH, straight chain or branched C2-C18alkenyl which is unsubstituted or substituted by â€”OH, C7-C15aralkyl, â€”CH2â€”CHOHâ€”E13 or glycidyl, E6 is hydrogen, straight or branched chain C1-C24alkyl which is unsubstituted or substituted by one or more OH, OE4 or NH2 groups, or â€”OE6 is â€”(OCH2CH2)wOH or â€”(OCH2CH2)wOE21where w is 1 to 12 and E21is alkyl of 1to 12 carbon atoms, E7 and E8 are independently hydrogen, alkyl of 1to 18 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, straight or branched chain C3-C18alkyl which is interrupted by â€”Oâ€”, â€”Sâ€”or â€”NE11â€”, C5-C12cycloalkyl, C6-C14aryl or C1-C3hydroxylalkyl, or E7 and E8 together with the N atom are a pyrrolidine, piperidine, piperazine or morpholine ring, E5 is â€”Xâ€”(Z)pâ€”Yâ€”E15 wherein X is â€”Oâ€” or â€”N(E16)â€”, Y is â€”Oâ€” or â€”N(E17)â€”, Z is C2-C12-alkylene, C4-C12-alkylene interrupted by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is C3-C12-alkylene, butenylene, butynylene, cyclohexylene or phenylene, each substituted by a hydroxyl group, m is zero, 1or 2, p is 1, or p is also zero when X and Y are â€”N(E16)â€” and â€”N(E17)â€”, respectively, E15 is a group â€”COâ€”C(E18)&boxH;C(H)E19 or, when Y is â€”N(E17)â€”, forms together with E17 a group â€”COâ€”CH&boxH;CHâ€”COâ€”, wherein E18 is hydrogen or methyl, and E19 is hydrogen, methyl or â€”COâ€”Xâ€”E20, wherein E20 is hydrogen, C1-C12-alkyl or a group of the formula â€ƒwherein the symbols E1, G2, X, Z, m and p have the meanings defined above, and E16 and E17 independently of one another are hydrogen, C1-C12-alkyl, C3-C12-alkyl interrupted by 1to 3 oxygen atoms, or is cyclohexyl or C7-C15aralkyl, and E16 together with E17 in the case where Z is ethylene, also forms ethylene, E11 is hydrogen, straight or branched chain C1-C18alkyl, C5-C12cycloalkyl, straight or branched chain C2-C18alkenyl, C6-C14aryl or C7-C15aralkyl, E12 is straight or branched chain C1-C18alkyl, straight or branched chain C3-C18alkenyl, C5-C10cycloalkyl, C6-C16aryl or C7-C15aralkyl, and E13 is H, straight chain or branched C1-C18alkyl which is substituted by â€”PO(OE12)2, phenyl which is unsubstituted or substituted by OH, C7-C15aralkyl or â€”CH2OE12, which comprises diazotizing a perfluoroalkyl substituted o-nitroaniline of formula II â€ƒusing concentrated sulfuric acid and an alkali metal nitrite or nitrosylsulfuric acid to form the corresponding diazonium salt of formula III which then couples with a phenol of formula IV to form a monoazobenzene compound of formula V reducing the monoazobenzene intermediate of formula V to the corresponding 2H-benzotriazole compound of formula I by conventional reduction means; and with the proviso that when concentrated sulfuric acid and alkali metal nitrite are used, E1 and E2 are alkyl of 1 to 4 carbon atoms, or E1 can also be hydrogen.