Patent ID: 6579328
Filing Date: 2003-06-17
Classification: C07B,C07D,C09K

Abstract:
A process for preparing a sterically hindered N-aryloxyamine of formula I, II, III, IV, V or VI which comprises reacting a sterically hindered nitroxyl compound of formula VII, VIII, IX, X or XI â€ƒwith a diazonium salt of an aromatic amine of formula XII, XIII or XIV â€ƒin the presence of a transition-metal catalyst wherein X is â€”CH2â€”, â€”Oâ€”, â€”Sâ€” or â€”NR8â€” where R8 is hydrogen or alkyl of 1 to 12 carbon atoms, R6 and R7 are independently alkyl of 1 to 8 carbon atoms, or R6 and R7 together are tetramethylene or pentamethylene, E2 is alkylene of 2 to 12 carbon atoms, G is chloro or â€”N(2-ethylhexyl)2, G1 is â€”CH2â€”, â€”COâ€” or â€”Oâ€”, R is hydrogen, alkyl of 1 to 18 carbon atoms, aralkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms, hydroxyl, carboxyl, amino, alkylamino of 1 to 18 carbon atoms, dialkylamino of 2 to 36 carbon atoms, oxo, alkylthio of 1 to 18 carbon atoms, alkoxy of 1 to 18 carbon atoms, aryloxy of 7 to 15 carbon atoms, benzoyloxy, alkylcarbonyloxy of 2 to 18 carbon atoms or alkylcarbonylamino of 2 to 18 carbon atoms, and R1 to R5 are independently hydrogen, halogen, nitro, cyano, alkyl of 1 to 18 carbon atoms, aralkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms, hydroxyl, carboxyl, alkylthio of 1 to 18 carbon atoms, alkoxy of 1 to 18 carbon atoms, aryloxy of 7 to 15 carbon atoms, alkylcarbonyloxy of 1 to 18 carbon atoms, alkylsulfonyl of 1 to 18 carbon atoms, arylsulfonyl of 6 to 15 carbon atoms, sulfo or â€”P(O)(OH)2 or â€”P(O)(OR6)2, or any two vicinal substituents connected together form a mono or polycyclic ring; or any two vicinal carboxyl groups can be joined to form an imide; or â€ƒwhere R, R6 and R7 are as defined above; or R3 is trifluoromethyl.