Patent GB-1489112-A (GB)
Title: Imidazolium salts
IPC: C07D233/60
Filed: 1975-01-22
Abstract: 1489112 Imidazolium salts JANSSEN PHARMACEUTICA NV 22 Jan 1975 [31 Jan 1974 19 Nov 1974] 2829/75 Heading C2C Novel salts I and hydrates thereof (in which A is phenyl, mono-, di- or tri-halophenyl, 1-6C alkyl-phenyl, 1-6C alkoxyphenyl, thienyl or halothienyl; B is benzyl, or phenethyl, either of which may be substituted by 1-3 halogen atoms, CN, 1-6C alkoxy, or one or two 1-6C alkyl, or B is 1-8C alkyl, 3-5C alkenyl, 3-5C alkynyl, mono- or di-nitrophenyl or mono- or di-aminophenyl; W is a pharmaceutically acceptable anion and D is 1-12C alkyl; (R is H or 1-5C alkyl; R<SP>1</SP> is H, 1-5C alkyl, halo, NO 2 , CF 3 , 1-5C alkoxy or phenoxy; a and m are 1 or 2 and n is 0, 1 or 2); (Ar is thienyl, halothienyl, or phenyl, optionally substituted by one or two of halo, 1-5C alkyl and 1-5C alkoxy and p is 1-4); (R<SP>2</SP> is H, halo, 1-5C alkyl or alkoxy, NO 2  or SO 2 NH 2 ; R<SP>3</SP> is H, halo, 1-5C alkyl or alkoxy or CN; p is 1-4); -CH(Ar<SP>1</SP>)(Ar<SP>1</SP>) (Ar<SP>1</SP> is phenyl or halo-phenyl); (R<SP>4</SP> is H, halo or 1-5C alkyl; a is 1 or 2); -(CH 2 ) q -Q-Ar<SP>2</SP> (Ar<SP>2</SP> is phenyl optionally substituted by one or two of halo, 1-5C alkyl, 1-5C alkoxy and allyl, or Ar<SP>2</SP> is naphthyl; Q is O or S; and q is 2 or 3); dihydrobenzofuran-2- yl - methyl; 5 - halo - dihydrobenzofuran- 2-yl-methyl; (R<SP>6</SP> is H, halo or 1-5C alkoxy and a is 1 or 2); -CH 2 CH : CHAr<SP>3</SP> (Ar<SP>3</SP> is phenyl, halophenyl or dihalophenyl) or -CH 2 -CO-CH 2 OAr<SP>3</SP>) are prepared by (a) reacting a compound II with a compound III (Z is a reactive ester group) or (b) reacting a compound IV with a compound V to give a compound I (W is Z), followed where necessary by exchanging the anion Z for another anion. 2 - Chloro - 6 - methyl - benzylanine (A) is prepared by reduction of 2-cyano-3-chlorotoluene. N - (2 - bromopropionyl) - 2 - chloro- 6-methylbenzylamine (B) is prepared by reaction of (A) with 2-bromopropionyl bromide. 3- Chloro - α,α,α - trifluoro - m - propionotoluidide (C) is prepared by reaction of 3-chloro-propionyl chloride with α,α,α-trifuoro-m-toluidine. N - benzyl - N - t - butyl - 2 - chloroacetamide (D) is prepared by reaction of N-benzyl-N-tbutylamine with 2-chloroacetyl chloride. 2- Bromomethyl - 2,3 - dihydro - 5 - fluorobenzofuran (E) is prepared by reaction of allyl bromide and 4-fluorophenol to give 4-allyloxy-fluorobenzene (F), rearrangement of (F) to give 2-allyl-4- fluorophenol (G), reaction of (G) with Ac 2 O to give 3 - allyl - 4 - acetoxy - fluorobenzene (H), reaction of (H) with Br 2  to give 3-(2,3-dibromopropyl) - 4 - acetoxy - fluorobenzene (J) and cyclization of (J). 3-Allyl-4-(3-bromo propoxy)- fluorobenzene (K) is prepared from 2-allyl-4- fluorophenol and 1,3 - dibromopropane. (α - Bromo - 5 - nitro - o - tolyl) butyl ether (L) is prepared by reaction of (5-nitro-o-tolyl) butyl ether with N-bromosuccinimide. 1- Chloro - 3 - (p - chlorophenoxy) - 2 - propanone (M) is prepared from 1-chloro-3-(p-chlorophenoxy) -propanol by oxidation with sodium dichromate. 1 - (p - Bromophenoxy) - 3 - chloro- 2-propanone (N) and 1-chloro-3-(2,4-dichlorophenoxy)-2-propanone (O) are prepared similarly to (M). 3 - (m - Chloro - phenoxy)propyl methane sulphonate (P) is prepared by reaction of 3 - (m - chlorophenoxy)propanol with mesyl chloride. p-(2-Iodoethyl)benzene sulphonamide (Q) is prepared from p-(2-chloroethyl)- benzene sulphonamide and NaI. Pharmaceutical compositions useful as antimicrobial, antibacterial and fungicidal agents comprise a compound I together with a suitable carrier.