CH503034A - Verfahren zur Herstellung von Halogenpyrimidinen - Google Patents
Verfahren zur Herstellung von HalogenpyrimidinenInfo
- Publication number
- CH503034A CH503034A CH1523567A CH1523567A CH503034A CH 503034 A CH503034 A CH 503034A CH 1523567 A CH1523567 A CH 1523567A CH 1523567 A CH1523567 A CH 1523567A CH 503034 A CH503034 A CH 503034A
- Authority
- CH
- Switzerland
- Prior art keywords
- chlorine
- fluorine
- bromine
- alkyl
- isocyanide
- Prior art date
Links
- 150000005694 halopyrimidines Chemical class 0.000 title claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000002825 nitriles Chemical class 0.000 claims abstract description 5
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical class Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- SXLDBFDRSPKHLY-UHFFFAOYSA-N trichloro(isocyano)methane Chemical compound ClC(Cl)(Cl)[N+]#[C-] SXLDBFDRSPKHLY-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 16
- GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- -1 chlorinated alkyl isocyanide dichlorides Chemical class 0.000 claims description 6
- DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 23
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 18
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- HCOGSNNNSJAJJN-UHFFFAOYSA-N 2,4,6-trichloro-5-(chloromethyl)pyrimidine Chemical compound ClCC1=C(Cl)N=C(Cl)N=C1Cl HCOGSNNNSJAJJN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 3
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- RIWNFZUWWRVGEU-UHFFFAOYSA-N isocyanomethylbenzene Chemical compound [C-]#[N+]CC1=CC=CC=C1 RIWNFZUWWRVGEU-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PXNJGLAVKOXITN-UHFFFAOYSA-N 2-(4-nitrophenyl)acetonitrile Chemical compound [O-][N+](=O)C1=CC=C(CC#N)C=C1 PXNJGLAVKOXITN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IXYRNHRNJWFINV-UHFFFAOYSA-N ClC1=NC(=C(C(=N1)Cl)C1=CC=C(C=C1)[N+](=O)[O-])Cl Chemical compound ClC1=NC(=C(C(=N1)Cl)C1=CC=C(C=C1)[N+](=O)[O-])Cl IXYRNHRNJWFINV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZALMZWWJQXBYQA-UHFFFAOYSA-N [N].[Cl] Chemical compound [N].[Cl] ZALMZWWJQXBYQA-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- FOTRKCAZUSJCQD-UHFFFAOYSA-N (methylsulfonyl)acetonitrile Chemical group CS(=O)(=O)CC#N FOTRKCAZUSJCQD-UHFFFAOYSA-N 0.000 description 1
- PNQJTGGOQNJSEL-UHFFFAOYSA-N 1,1,1,2,2-pentachloro-2-isocyanoethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)[N+]#[C-] PNQJTGGOQNJSEL-UHFFFAOYSA-N 0.000 description 1
- QMYVLWDYEJFVHW-UHFFFAOYSA-N 1,2-dichloro-4-(isocyanomethyl)benzene Chemical compound ClC1=CC=C(C[N+]#[C-])C=C1Cl QMYVLWDYEJFVHW-UHFFFAOYSA-N 0.000 description 1
- RZELGCMBQAPXRI-UHFFFAOYSA-N 1-isocyanododecane Chemical compound CCCCCCCCCCCC[N+]#[C-] RZELGCMBQAPXRI-UHFFFAOYSA-N 0.000 description 1
- WDNIHYDTZZOFLR-UHFFFAOYSA-N 2,2,2-tribromoacetonitrile Chemical compound BrC(Br)(Br)C#N WDNIHYDTZZOFLR-UHFFFAOYSA-N 0.000 description 1
- BKSBZHFVGCOTKR-UHFFFAOYSA-N 2,2-dibromo-2-nitroacetonitrile Chemical compound [O-][N+](=O)C(Br)(Br)C#N BKSBZHFVGCOTKR-UHFFFAOYSA-N 0.000 description 1
- GNOYKMLCUATEDC-UHFFFAOYSA-N 2,2-dichloro-2-ethoxyacetonitrile Chemical compound C(C)OC(C#N)(Cl)Cl GNOYKMLCUATEDC-UHFFFAOYSA-N 0.000 description 1
- MOQSQJQIQAJCRW-UHFFFAOYSA-N 2,2-dichloro-2-nitroacetonitrile Chemical compound ClC(C#N)([N+](=O)[O-])Cl MOQSQJQIQAJCRW-UHFFFAOYSA-N 0.000 description 1
- HDTAUMIOSWQZRW-UHFFFAOYSA-N 2,2-dichloro-2-phenylacetonitrile Chemical compound N#CC(Cl)(Cl)C1=CC=CC=C1 HDTAUMIOSWQZRW-UHFFFAOYSA-N 0.000 description 1
- VTSWSQGDJQFXHB-UHFFFAOYSA-N 2,4,6-trichloro-5-methylpyrimidine Chemical compound CC1=C(Cl)N=C(Cl)N=C1Cl VTSWSQGDJQFXHB-UHFFFAOYSA-N 0.000 description 1
- FEWAAURGHSVADC-UHFFFAOYSA-N 2-(2,3,4-trichlorophenyl)acetonitrile Chemical compound ClC1=CC=C(CC#N)C(Cl)=C1Cl FEWAAURGHSVADC-UHFFFAOYSA-N 0.000 description 1
- MRDUURPIPLIGQX-UHFFFAOYSA-N 2-(2-chlorophenyl)acetonitrile Chemical compound ClC1=CC=CC=C1CC#N MRDUURPIPLIGQX-UHFFFAOYSA-N 0.000 description 1
- YPRFCQAWSNWRLM-UHFFFAOYSA-N 2-(2-nitrophenyl)acetonitrile Chemical compound [O-][N+](=O)C1=CC=CC=C1CC#N YPRFCQAWSNWRLM-UHFFFAOYSA-N 0.000 description 1
- QWZNCAFWRZZJMA-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1Cl QWZNCAFWRZZJMA-UHFFFAOYSA-N 0.000 description 1
- MFHFWRBXPQDZSA-UHFFFAOYSA-N 2-(4-bromophenyl)acetonitrile Chemical compound BrC1=CC=C(CC#N)C=C1 MFHFWRBXPQDZSA-UHFFFAOYSA-N 0.000 description 1
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
- WZSOEUAQKKEHFE-UHFFFAOYSA-N 2-chloro-2-phenylacetonitrile Chemical compound N#CC(Cl)C1=CC=CC=C1 WZSOEUAQKKEHFE-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical class [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- JNAYPRPPXRWGQO-UHFFFAOYSA-N 2-chloropropanenitrile Chemical compound CC(Cl)C#N JNAYPRPPXRWGQO-UHFFFAOYSA-N 0.000 description 1
- UMCQAGDGGSOQGK-UHFFFAOYSA-N 2-ethylsulfonylacetonitrile Chemical compound CCS(=O)(=O)CC#N UMCQAGDGGSOQGK-UHFFFAOYSA-N 0.000 description 1
- QKPVEISEHYYHRH-UHFFFAOYSA-N 2-methoxyacetonitrile Chemical compound COCC#N QKPVEISEHYYHRH-UHFFFAOYSA-N 0.000 description 1
- DWBOSISZPCOPFS-UHFFFAOYSA-N 2-nitroacetonitrile Chemical compound [O-][N+](=O)CC#N DWBOSISZPCOPFS-UHFFFAOYSA-N 0.000 description 1
- OPXYNEYEDHAXOM-UHFFFAOYSA-N 3-oxobutanenitrile Chemical compound CC(=O)CC#N OPXYNEYEDHAXOM-UHFFFAOYSA-N 0.000 description 1
- UZVRXBTXEACDQE-UHFFFAOYSA-N 4,5,6-trichloro-2-phenylpyrimidine Chemical compound ClC1=C(Cl)C(Cl)=NC(C=2C=CC=CC=2)=N1 UZVRXBTXEACDQE-UHFFFAOYSA-N 0.000 description 1
- NDSBDLSWTGLNQA-UHFFFAOYSA-N Dibromoacetonitrile Chemical compound BrC(Br)C#N NDSBDLSWTGLNQA-UHFFFAOYSA-N 0.000 description 1
- STZZWJCGRKXEFF-UHFFFAOYSA-N Dichloroacetonitrile Chemical compound ClC(Cl)C#N STZZWJCGRKXEFF-UHFFFAOYSA-N 0.000 description 1
- KLMUIUZICXCPCE-UHFFFAOYSA-N N=C=O.Cl.Cl Chemical compound N=C=O.Cl.Cl KLMUIUZICXCPCE-UHFFFAOYSA-N 0.000 description 1
- XHIHZCRYMKXXDC-UHFFFAOYSA-N [dichloro(isocyano)methyl]benzene Chemical compound [C-]#[N+]C(Cl)(Cl)C1=CC=CC=C1 XHIHZCRYMKXXDC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- DRUKSYADHNANTP-UHFFFAOYSA-N chloro(isocyano)methane Chemical compound ClC[N+]#[C-] DRUKSYADHNANTP-UHFFFAOYSA-N 0.000 description 1
- AJEHNBIPLQJTNU-UHFFFAOYSA-N cyanomethyl acetate Chemical compound CC(=O)OCC#N AJEHNBIPLQJTNU-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- ZRKSVHFXTRFQFL-UHFFFAOYSA-N isocyanomethane Chemical compound C[N+]#[C-] ZRKSVHFXTRFQFL-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical class CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Movable Scaffolding (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967F0052193 DE1670854B2 (de) | 1967-04-20 | 1967-04-20 | Verfahren zur herstellung von 2,4,6- trichlorpyrimidinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH503034A true CH503034A (de) | 1971-02-15 |
Family
ID=7105251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1523567A CH503034A (de) | 1967-04-20 | 1967-10-31 | Verfahren zur Herstellung von Halogenpyrimidinen |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT281034B (en。) |
| BE (1) | BE707203A (en。) |
| CH (1) | CH503034A (en。) |
| DE (1) | DE1670854B2 (en。) |
| DK (1) | DK117492B (en。) |
| ES (1) | ES347176A1 (en。) |
| GB (1) | GB1156408A (en。) |
| NL (1) | NL6715452A (en。) |
| NO (1) | NO121341B (en。) |
| SE (1) | SE332989B (en。) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI895821A7 (fi) * | 1988-12-07 | 1990-06-08 | The Wellcome Foundation Ltd | Farmaseuttisesti aktivisia CNS-yhdisteitä |
-
1967
- 1967-04-20 DE DE1967F0052193 patent/DE1670854B2/de active Granted
- 1967-10-31 CH CH1523567A patent/CH503034A/de not_active IP Right Cessation
- 1967-11-02 GB GB4990067A patent/GB1156408A/en not_active Expired
- 1967-11-08 DK DK556867A patent/DK117492B/da unknown
- 1967-11-14 NL NL6715452A patent/NL6715452A/xx unknown
- 1967-11-15 ES ES347176A patent/ES347176A1/es not_active Expired
- 1967-11-20 SE SE1594067A patent/SE332989B/xx unknown
- 1967-11-28 BE BE707203D patent/BE707203A/xx unknown
- 1967-11-30 NO NO17076367A patent/NO121341B/no unknown
- 1967-12-04 AT AT1093967A patent/AT281034B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE332989B (en。) | 1971-03-01 |
| DE1670854A1 (de) | 1971-03-18 |
| DK117492B (da) | 1970-05-04 |
| ES347176A1 (es) | 1969-01-16 |
| BE707203A (en。) | 1968-05-28 |
| NO121341B (en。) | 1971-02-15 |
| DE1670854B2 (de) | 1977-04-28 |
| GB1156408A (en) | 1969-06-25 |
| AT281034B (de) | 1970-05-11 |
| NL6715452A (en。) | 1968-10-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0038987B1 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| DE2614242B2 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| DE2708189C2 (de) | Verfahren zur Herstellung von Phenylglyoxylsäureestern | |
| CH597199A5 (en) | 3-Phenyl pyridaz-6-ones prodn. | |
| DE2737210C2 (de) | Verfahren zur Herstellung von Nitrilen | |
| CH503034A (de) | Verfahren zur Herstellung von Halogenpyrimidinen | |
| DE2815541A1 (de) | Verfahren zur herstellung von carbonsaeureanhydriden | |
| EP0173191A2 (de) | 5,5-Dichlor-4,5-dihydro-6-hydroxy-2-trichlormethyl-pyrimidin-4-on, ein Verfahren zu seiner Herstellung und seine Verwendung | |
| DE1770774A1 (de) | Verfahren zur Herstellung von Halogenpyrimidinen | |
| DE2708183B2 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| DE2756438A1 (de) | Verfahren zur herstellung von 4,6-dihalogen-triazinen | |
| EP0137175B1 (de) | Verfahren zur Herstellung von benzokondensierten, tetrachlorierten, heterocyclischen Verbindungen | |
| DE2125229C3 (de) | Verfahren zur Herstellung von Chinazolinen | |
| DE2221771C3 (de) | Verfahren zur Herstellung von α-Iminonitrilen | |
| EP0043490B1 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| EP0089485A2 (de) | Verfahren zur Herstellung von 5-Chlor-1H-tetrazol-1-carbonsäureestern sowie Verfahren zur Herstellung der erforderlichen Dichlorisonitril-carbonsäureester | |
| DE1670854C3 (de) | Verfahren zur Herstellung von 2,4,6-Trichlorpyrimidinen | |
| EP0023033A1 (de) | 2.4.6-Trihalogen-pyrimidin-5-carbonsäurehalogenide und Verfahren zu ihrer Herstellung | |
| EP0173153B1 (de) | Neue benzokondensierte, fluorierte, heterocyclische Verbindungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE3033122A1 (de) | Verfahren zur herstellung von 1-brom-3,5-dichlorbenzol | |
| EP0273409A1 (de) | Neue Nitrohaloalkoxybenzole, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1545843A1 (de) | Verfahren zur Herstellung substituierter Pyrimidine | |
| EP0132681A1 (de) | Verfahren zur Herstellung von Fluorcarbonsäuren | |
| EP0133663A1 (de) | Neue Pyrimidine und ein Verfahren zur Herstellung von Pyrimidinen | |
| DE2445681A1 (de) | Verfahren zur herstellung von 3-phenylpyridazonen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |