Process for the preparation of benzotriazoles

A process for the preparation of a compound of formula I

• 73
• wherein
• R1, R2, R3, R4, R5, R6, R71 R8 and R9 are each independently of the others hydrogen, halogen, —SO3H, —SO3−Ma+, hydroxy, carboxy, cyano, nitro, C1-C25alkyl, C1-C25alkyl substituted by halogen, hydroxy, carboxy, cyano, C1-C18alkoxycarbonyl, C1-C4alkoxy or by amino;
• C2-C24-alkenyl, C7-C9phenylalkyl, unsubstituted or C1-C4alkyl-substituted phenyl, unsubstituted or C1-C4alkyl-substituted C5-C8cycloalkyl;
• C1-C18alkoxy, C1-C18alkylthio, C1-C18alkylsulfonyl, unsubstituted or C1-C4alkyl-substituted phenylsulfonyl, unsubstituted or C1-C4alkyl-substituted phenylthio;
• amino, C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C25alkanoyl, C1-C25alkoxycarbonyl, C1-C26alkanoyloxy, C1-C25alkanoylamino, C3-C25alkyl interrupted by oxygen, sulfur or by
• 74
• C3-C25alkoxy interrupted by oxygen, sulfur or by
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• C3-C25alkanoyloxy interrupted by oxygen, sulfur or by
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• C3-C25alkoxycarbonyl interrupted by oxygen, sulfur or by
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• C6-C9cycloalkoxycarbonyl, C6-C9cycloalkylcarbonyloxy, unsubstituted or C1-C12alkyl-substituted benzoyloxy;
• —(CH2)p—COR11 or —(CH2)qOH, or, further, the radicals R6 and R7 or the radicals R7 and R8 or the radicals R8 and R9, together with the carbon atoms to which they are bonded, form a benzo ring, R3 in addition is a radical of formula II
• 78
• and R6 in addition is a radical of formula III
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• R10 is hydrogen or C1-C8alkyl,
• R11 is hydroxy,
• 4 [ - o - ⁢ 1 r ⁢ M b r + ] ,
• C1-C18alkoxy, —O[Brketopenst]CH2CH2—O[Brketclosest]mH,
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• a radical of formula IV
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• R12 is —SO—, —SO2—, —SO—R16—SO—, —SO2—R16—SO2—,
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• R13 and R14 are each independently of the other hydrogen or C1-C18alkyl,
• R15 is —O—R17—O—,
• R16 is C2-C12alkylene, C5-C12cycloalkylene, or C8-C12alkylene interrupted or terminated by cyclohexylene;
• R17 is C2-C12alkylene, or C4-C12alkylene interrupted by oxygen, sulfur or by
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• Ma is a monovalent metal cation,
• Mb is an r-valent metal cation,
• m is an integer from 1 to 20,
• p is 0, 1 or 2,
• q is 1, 2, 3, 4, 5 or 6, and
• r is 1, 2 or 3,
• which process comprises reacting a compound of formula V
• 84
• wherein
• R1, R2, R3, R4, R5, R6, R7, R8 and R9 are as defined hereinbefore, R3 in addition being a radical of formula VI
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• R6 in addition being a radical of formula VII
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• and R11 in addition being a radical of formula VIII
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• R18 is halogen, nitro, —N+═N X−, R19—S+—R19 X−, —SO3H,
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• R19 is C1-C18alkyl, unsubstituted or C1-C4alkyl-substituted phenyl;
• or unsubstituted or C1-C4alkyl-substituted C5-C8cycloalkyl,
• R19 is C1-C18alkyl, unsubstituted or C1-C4alkyl-, halo- or nitro-substituted phenyl;
• unsubstituted or C1-C4alkyl-substituted C5-C8cycloalkyl;
• or fluorine-substituted C1-C18alkyl, and
• X− is chloride, bromide, iodide, hydroxide, nitrate or nitrite,
• with an azide compound of formula IX
• Mn+(N3−)n (IX)
• wherein
• M is an n-valent metal cation,
• 89
• or P+(R25)4,
• R21, R22, R23 and R24 are each independently of the others hydrogen or C1-C18alkyl,
• R25 is C1-C18alkyl, and
• n is 1, 2 or 3.