Method for the production of 2-(2-ethoxyphenyl)-substituted imidazotriazinones
View Patent ↗The invention relates to a method for the production of 2-phenyl-substituted imidazotriazinones of general formula (I), comprising the reaction of compounds of formula (II) with compounds of formula (III) and subsequent reaction with iodine or bromine, then with a metal cyanide and reaction with an acid.
1. Process for preparing a compound of the formula (I)
in which
R 1 represents hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms,
R 2 represents straight-chain alkyl having up to 4 carbon atoms,
R 3 and R 4 are identical or different and represent hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms, or represent straight-chain or branched alkoxy having up to 6 carbon atoms,
comprising reaction of a compound of the formula (II)
in which R 2 , R 3 and R 4 have the meaning indicated above, with a compound of the formula (III)
in which
R 1 has the meaning indicated above,
X represents halogen;
in the presence of a base and, where appropriate, of a metal iodide in an organic solvent to give a compound of the formula (IV)
in which R 1 , R 2 , R 3 and R 4 have the meaning indicated above, and subsequent reaction
[A] with iodine in the presence of a base in a solvent, subsequent reaction with a metal cyanide in a solvent and reaction with an acid
or
[B] with bromine in acidic medium, subsequent reaction with a metal cyanide in a solvent and reaction with an acid.
2. Process according to claim 1 , characterized in that
R 1 denotes straight-chain alkyl having up to 4 carbon atoms,
R 2 denotes straight-chain alkyl baiting up to 4 carbon atoms,
R 3 and R 4 denote, identically or differently from one another, hydrogen or straight-chain or branched alkoxy having up to 4 carbon atoms.
3. Process according to claim 1 , characterized in that
R 1 denotes methyl or ethyl,
R 2 denotes n-propyl,
R 3 denotes hydrogen,
R 4 denotes ethoxy.
4. Process according to claim 1 , characterized in that X in the compound of the formula (III) represents chlorine.
5. Process according to claim 1 , characterized in that the reaction of the compounds of the formula (II) and (III) is carried out in the presence of potassium iodide and triethylamine.
6. Process according to claim 1 , characterized in that the reaction of the compounds of the formula (II) and (III) is carried out in the presence of potassium carbonate.
7. Process according to claim 1 , characterized in that the reaction of a compound of the formula (IV) with iodine is carried out with the exclusion of light in the presence of sodium carbonate and subsequently with CuCN in pyridine.
8. Process according to claim 1 , characterized in that the reaction of a compound of the formula (IV) with bromine is carried out in the presence of acetic acid and subsequently with CuCN in pyridine in the presence of potassium iodide.
9. Process according to claim 1 , characterized in that sulphuric acid is used as the acid in the concluding step.
10. Process according to claim 1 , characterized in that a compound of the formula (II) is prepared by reacting a compound of the formula (V)
in which
R 1 and R 4 have the meaning indicated in claim 1 , with a compound of the formula (VI)
in which
R 2 has the meaning indicated in claim 1 ,
R 5 represents C 1-6 -alkyl,
in an organic solvent in the presence of a base.