Patent GB-1493383-A (GB)
Title: Diphenyl pyrazoline derivatives
IPC: C07D231/06
Filed: 1974-01-29
Abstract: 1493383 Diphenylpyrazoline derivatives SANDOZ PRODUCTS Ltd 28 Jan 1975 [29 Jan 1974 3 May 1974] 04087/74 and 19663/74 Heading C2C Novel optical brightening agents, being 1,3- diphenyl substituted pyrazolines and having, in the 4- or 5-position of the pyrazoline ring, a sulpho group in free acid or salt form and in which the phenyl rings may be substituted, particularly compounds which, in free acid form, have Formula I in which either R 1 , R 2  and R 3 , independently, each signifies hydrogen, halogen, C 1-8  alkyl, C 1-4  alkoxy, cyano or -SO 3 H, or two of R 1 , R 2  and R 3 , together, signify a methylenedioxy radical, the other having one of the above significances, or one of R 1 , R 2  and R 3  signifies a phenyl radical, unsubstituted or substituted by one or two substituents selected from C 1-4  alkyl, C 1-4  alkoxy, halogen and -SO 3 H, the other two each having one of the significances first mentioned above; with the proviso that ring A bears no more than one substituent selected from cyano and -SO 3 H, R 4  signifies hydrogen, C 1-8  alkyl, unsubstituted phenyl or phenyl substituted by one or two substituents selected from halogen, C 1-4  alkyl, C 1-4  alkoxy and -SO 3 H, R 5  signifies hydrogen, halogen, C 1-4  alkyl, C 1-4  alkoxy or cyano, either U signifies -SO 3 H, -CO 2 R 6 , -CONR 7 R 8 , or -SO 2 R 9 , in which R 6  signifies hydrogen; C 1-4  alkyl, unsubstituted or substituted by a C 1-4  alkyl, C 1-4  alkoxy, -SO 3 H, -COOH, C 1-4  alkoxycarbonyl, aminocarbonyl, mono- or di- C 1-4  alkylaminocarbonyl, aminosulphonyl or a mono- or di-C 1-4  alkylaminosulphonyl group; or phenyl, unsubstituted or substituted by one or two substituents selected from C 1-4  alkyl, C 1-4  alkoxy, -SO 3 H, -COOH, C 1-4  alkoxycarbonyl, aminocarbonyl, and mono- and di- C 1-4  alkylaminocarbonyl, R 7  and R 8 , independently, each have one of the significances of R 6 , above, provided that both do not simultaneously signify an unsubstituted or substituted phenyl, R 9  signifies hydrogen; C 1-4  alkyl, unsubstituted or substituted by a (i) hydroxy group; (ii) C 1-4  alkyl group; (iii) C 1-4  alkoxy group, unsubstituted or substituted by a C 1-4  alkoxy, -SO 3 H, -COOH, C 1-4  alkoxycarbonyl, aminocarbonyl or C 1-4  mono- or di-alkylaminocarbonyl group; (iv) -SO 3 H group; (v) -SO 2 NR 10 R 11  group, in which R 10  and R 11  independently, signify hydrogen or C 1-4  alkyl; (vi) -COOR 12  group, in which R 12  signifies hydrogen, C 1-4  alkyl, unsubstituted or substituted by -SO 3 H, or a phenyl group unsubstituted or substituted by one or two groups selected from C 1-4  alkyl and -SO 3 H, or a (vii) -CONR 13 R 14  group, in which R 13  and R 14 , independently, each have one of the significances of R 12 , above; provided that both do not simultaneously signify an unsubstituted or substituted phenyl; a C 2-4  alkenyl group; a C 1-4  alkoxy group; or a phenyl group, unsubstituted or substituted by one or two substituents selected from C 1-4  alkyl, C 1-4  alkoxy, -SO 3 H, -COOH, C 1-4 -alkoxycarbonyl, aminocarbonyl and mono- and di-C 1-4  alkylamino-carbonyl radicals; or U has one of the significances of R 5 , above, are prepared by (a) reacting a 2- or 3-sulphopropiophenone substituted in 3-position with halogen, NH 2 , dialkylamino, morpholino, piperidino or pyrrolidino with a phenylhydrazine, or (b) reacting a diphenylnitrile imine (which may be prepared in situ from an α-chlorobenzaldehyde and a base) with a vinylsulphonic acid or salt. 3 - (4<SP>11 </SP>- morpholino) - [4<SP>1</SP> - chloro - 2<SP>1</SP>,5<SP>1</SP>- dimethylpropiophenone]-2-sulphonate and 3-(4<SP>11</SP>- morpholino) - [4<SP>1</SP> - chloropropiophenone] - 2- sulphonate (internal salts) are prepared from morpholine hydrochloride, paraformaldehyde and the appropriate acetophenone-2-sulphonic acid.