BE623053A - - Google Patents

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Publication number

BE623053A

BE623053A BE623053DA BE623053A BE 623053 A BE623053 A BE 623053A BE 623053D A BE623053D A BE 623053DA BE 623053 A BE623053 A BE 623053A

Authority

BE

Belgium

Prior art keywords

group

substituted

preparation

general formula

representing

Prior art date

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• 238000000034 method Methods 0.000 claims description 14
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
• 150000003568 thioethers Chemical class 0.000 claims description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 239000007858 starting material Substances 0.000 claims description 5
• YRNOMHVNGUKADJ-UHFFFAOYSA-N 5h-pyrido[2,3-b][1,4]benzothiazine Chemical group C1=CC=C2NC3=CC=CC=C3SC2=N1 YRNOMHVNGUKADJ-UHFFFAOYSA-N 0.000 claims description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
• 229910021529 ammonia Inorganic materials 0.000 claims description 4
• DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 4
• 125000003277 amino group Chemical group 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000001931 aliphatic group Chemical group 0.000 claims description 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 238000006243 chemical reaction Methods 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 2
• 239000001257 hydrogen Substances 0.000 claims description 2
• 125000002560 nitrile group Chemical group 0.000 claims description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
• 241001614020 Asaphes Species 0.000 claims 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
• 125000002252 acyl group Chemical group 0.000 claims 1
• 125000004414 alkyl thio group Chemical group 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 description 3
• BFGSDHMSRIJNEV-UHFFFAOYSA-N 3-chloro-5H-pyrido[2,3-b][1,4]benzothiazine Chemical compound ClC1=CC=2NC3=CC=CC=C3SC2N=C1 BFGSDHMSRIJNEV-UHFFFAOYSA-N 0.000 description 2
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• 238000007363 ring formation reaction Methods 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• 239000011593 sulfur Substances 0.000 description 2
• 229910052717 sulfur Inorganic materials 0.000 description 2
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
• UKDZROJJLPDLDO-UHFFFAOYSA-N 10h-pyrido[3,2-b][1,4]benzothiazine Chemical compound C1=CN=C2NC3=CC=CC=C3SC2=C1 UKDZROJJLPDLDO-UHFFFAOYSA-N 0.000 description 1
• 229910015900 BF3 Inorganic materials 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
• 125000005035 acylthio group Chemical group 0.000 description 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
• 125000004432 carbon atom Chemical group C* 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• HUDSSSKDWYXKGP-UHFFFAOYSA-N n-phenylpyridin-2-amine Chemical compound C=1C=CC=NC=1NC1=CC=CC=C1 HUDSSSKDWYXKGP-UHFFFAOYSA-N 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• 239000000575 pesticide Substances 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• 229940127557 pharmaceutical product Drugs 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 235000015320 potassium carbonate Nutrition 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 150000003222 pyridines Chemical class 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 239000001117 sulphuric acid Substances 0.000 description 1
• 235000011149 sulphuric acid Nutrition 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 235000005074 zinc chloride Nutrition 0.000 description 1
• 239000011592 zinc chloride Substances 0.000 description 1