Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/30—Halogen atoms or nitro radicals

Definitions

• the present invention relates to a process for the preparation of 4,6-dichloropyrimidine from 4-chloro-6-methoxypyrimidine.
• 4,6-dichloropyrimidine is a valuable intermediate for the production of crop protection products.
• Ci-Ci Q- alkyl or Cg-Ci Q- aryl which may be substituted by up to 5 identical or different substituents from the group fluorine, chlorine, bromine, C 1 -C 4 -alkyl and C ⁇ -C ⁇ alkoxy can,
• n stand for zero or 1.
• Preferred sulfur-containing chlorinating agents are SOCI2 and SO2CI2, preferred phosphorus compounds triphenylphosphine and triphenylphosphine oxide.
• phosphorus compounds of the formula (I) Based on 1 mol of sulfur-containing chlorinating agents, for example 0.01 to 1 mol of phosphorus compounds of the formula (I) can be used. This amount is preferably 0.02 to 0.25, particularly preferably 0.05 to 0.1 mol.
• the process according to the invention is preferably carried out in the presence of a solvent.
• a solvent for example, aromatic solvents such as toluene, xylenes, chlorobenzene, dichlorobenzenes, chlorotoluenes, benzonitrile and benzotrifluoride, nitrogen-containing solvents such as N-methylpyrrolidone, dimethylformamide, dimethylacetamide and cyclic ureas and oxygen-containing solvents such as ethers, in particular higher-boiling ethers, are suitable. Mixtures of solvents can also be used.
• the process according to the invention can be carried out, for example, at temperatures in the range from 50 to 200.degree. 75 to 175 ° C., in particular 100 to 150 ° C., are preferred.
• the pressure is not critical. Only if you want to use solvents that boil at normal pressure below the desired reaction temperature, it is advisable to work under increased pressure so that the solvent is at least partially in liquid form.
• the pressure can range, for example, from 0.1 to 5 bar.
• the process is preferably carried out at atmospheric pressure, particularly preferably with a solvent which boils under reflux at the desired reaction temperature under atmospheric pressure.
• the process according to the invention can be carried out batchwise and continuously.
• 4-chloro-6-methoxypyrimidine, the phosphorus compound and a solvent are introduced, the mixture is heated to the reaction temperature and then the sulfur-containing chlorinating agent is metered in, if appropriate in several portions.
• the reaction mixture present after the reaction can be e.g. work up by distilling it over a column, if necessary under reduced pressure.
• the process according to the invention can be used to convert 4-chloro-6-methoxypyrimidine into 4,6-dichloropyrimidine in a simple manner.
• the conversion succeeds in
• Example 1 was repeated, but 200 ml of a mixture of isomeric xylenes were used instead of chlorobenzene and the process was carried out at 135.degree.
• the HPLC analysis showed a yield of 4,6-dichloropyrimidine of 93.6% and unreacted 4-chloro-6-methoxypyrimidine in an amount of 2.6% of the feed.
• Example 1 was repeated, but instead of thionyl chloride, 49.2 g of a mixture of 3 mols of SOO2 and 1 mol of SO2Cl2 were added dropwise in 1 hour and after 6

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
• Pyridine Compounds (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Plural Heterocyclic Compounds (AREA)

Applications Claiming Priority (3)

Publications (1)

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Family Applications (1)

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Family Cites Families (2)

• 1999
  • 1999-08-13 DE DE19938500A patent/DE19938500A1/de not_active Withdrawn
• 2000
  • 2000-07-31 AU AU61612/00A patent/AU6161200A/en not_active Abandoned
  • 2000-07-31 JP JP2001517508A patent/JP2003507370A/ja active Pending
  • 2000-07-31 US US10/069,089 patent/US6525198B1/en not_active Expired - Fee Related
  • 2000-07-31 EP EP00948019A patent/EP1210337A1/de not_active Withdrawn
  • 2000-07-31 WO PCT/EP2000/007401 patent/WO2001012610A1/de not_active Application Discontinuation
  • 2000-07-31 CA CA002388607A patent/CA2388607A1/en not_active Abandoned

Non-Patent Citations (1)

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