Patent GB-1195324-A (GB)
Title: 2,4,5-Triphenyl (and Substituted Triphenyl)-3-Acetonitriles of Pyrrole, Furan and Thiophene
IPC: C07D207/34
Filed: 1968-02-05
Abstract: 1,195,324. 2,4,5 - Triphenyl-pyrrole, thiophene or furan-acetonitrile derivatives. UPJOHN CO. 5 Feb., 1968 [21 Feb., 1967], No. 5673/68. Heading C2C. Novel compounds of the Formula I, wherein X represents an oxygen or sulphur atom or a methyl-substituted or an unsubstituted imino group; R 1 , R 2  and R 3  represent a hydrogen or halogen atom or a C 1-4  alkyl, C 1-4  alkoxy or trifluoromethyl group and R represents a hydrogen atom or, when X represents an imino group, R may also represent a methyl group, are prepared, where X represents an imino group, by reacting a compound of the Formula II with formaldehyde or acetaldehyde with a dialkylamine converting the resultant tertiary amine of the Formula III to a quaternary ammonium halide with an alkyl halide and treating the latter with an alkali metal cyanide; where X can have any of the meanings defined above, by reacting a compound of the Formula IIa with formaldehyde and HCl or HBr to give its 3-halomethyl derivative and reacting the latter with an alkali metal cyanide; and where R represents a hydrogen atom by brominating a 3-methyl derivative of the Formula IV with N-bromosuccinimide and reacting the 3-bromomethyl compound produced with an alkali metal cyanide, or by chlorinating a 3-hydroxymethyl compound of the Formula V and reacting the 3-chloromethyl product with an alkali metal cyanide. 3-Hydroxymethyl derivatives of the Formula V may be prepared by reacting a compound of the Formula IIa with bromine to give the 3-bromo derivative, reacting the latter with magnesium and reacting the resultant Grignard compound with formaldehyde. 2,3 - Bis - (p - methoxyphenyl) - 5 - phenylpyrrole may be prepared by reacting ethyl benzoylacetate with 2 - amino - 4<SP>1 </SP>- methoxy - 2 (p - methoxyphenyl) acetophenone hydrochloride and reacting the resulting ethyl 4,5-bis- (p - methoxyphenyl) - 2 - phenylpyrrole - 3 - carboxylate with sodium hydroxide. 2,3,5-Triphenylpyrrole may be prepared by reacting benzoin with acetophenone and reacting the resulting 1,2,4-triphenyl-1,4-butanedione with formamide. 2,3 - Bis - (p - methoxyphenyl) - 1 - methyl - 5 - phenylpyrrole may be prepared by reacting anisoin and reacting the product with methyl formamide. Other 2,3,5 - triphenylpyrrole intermediates may be prepared by methods similar to those described above. 2,3 - Bis - (p - methoxyphenyl) - 5 - phenylfuran may be prepared by reacting desoxyanisoin with pyrrolidine and reacting the product with phenacyl bromide to give the desired product together with 1,2-bis-(p-methoxyphenyl) - 4 - phenyl - 1,4 - butanedione; or by reacting anisoin with acetophenone and reacting the resulting 1,2-bis-(p-methoxyphenyl)-4-phenyl. 1,4-butanedione with concentrated sulphuric acid. 2,3,5 - Tri - (p - anisyl) furan may be prepared by reacting anisoin with p-methoxyacetophenone and treating the resulting 1,2,4-tri-(panisyl)-1,4-butanedione with concentrate sulphuric acid. Therapeutic compositions with anti-inflammatory, analgesic and antipyretic properties in forms suitable for oral, parenteral and topical application comprise compounds of the Formula I together with a suitable carrier.