DE1670854B2 - Verfahren zur herstellung von 2,4,6- trichlorpyrimidinen - Google Patents
Verfahren zur herstellung von 2,4,6- trichlorpyrimidinenInfo
- Publication number
- DE1670854B2 DE1670854B2 DE1967F0052193 DEF0052193A DE1670854B2 DE 1670854 B2 DE1670854 B2 DE 1670854B2 DE 1967F0052193 DE1967F0052193 DE 1967F0052193 DE F0052193 A DEF0052193 A DE F0052193A DE 1670854 B2 DE1670854 B2 DE 1670854B2
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- trichloropyrimidines
- chlorine
- theory
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical class ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229910052801 chlorine Chemical group 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- SXLDBFDRSPKHLY-UHFFFAOYSA-N trichloro(isocyano)methane Chemical compound ClC(Cl)(Cl)[N+]#[C-] SXLDBFDRSPKHLY-UHFFFAOYSA-N 0.000 description 4
- GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KMPDRUUXTSYMJD-UHFFFAOYSA-N 2,4,6-trichloro-5-ethylpyrimidine Chemical compound CCC1=C(Cl)N=C(Cl)N=C1Cl KMPDRUUXTSYMJD-UHFFFAOYSA-N 0.000 description 1
- YMCHZJBZJNKSHU-UHFFFAOYSA-N 2,4,6-trichloro-5-phenylpyrimidine Chemical compound ClC1=NC(Cl)=NC(Cl)=C1C1=CC=CC=C1 YMCHZJBZJNKSHU-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
- MFHFWRBXPQDZSA-UHFFFAOYSA-N 2-(4-bromophenyl)acetonitrile Chemical compound BrC1=CC=C(CC#N)C=C1 MFHFWRBXPQDZSA-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical class [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- STZZWJCGRKXEFF-UHFFFAOYSA-N Dichloroacetonitrile Chemical compound ClC(Cl)C#N STZZWJCGRKXEFF-UHFFFAOYSA-N 0.000 description 1
- -1 Trichloroacetonilril Chemical compound 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000005694 halopyrimidines Chemical class 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
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical class CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000002904 solvent Substances 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)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967F0052193 DE1670854B2 (de) | 1967-04-20 | 1967-04-20 | Verfahren zur herstellung von 2,4,6- trichlorpyrimidinen |
| CH1523567A CH503034A (de) | 1967-04-20 | 1967-10-31 | Verfahren zur Herstellung von Halogenpyrimidinen |
| GB4990067A GB1156408A (en) | 1967-04-20 | 1967-11-02 | Process for the Production of Halopyrimidines |
| DK556867A DK117492B (da) | 1967-04-20 | 1967-11-08 | Fremgangsmåde til fremstilling af halogenpyrimidiner. |
| NL6715452A NL6715452A (is") | 1967-04-20 | 1967-11-14 | |
| ES347176A ES347176A1 (es) | 1967-04-20 | 1967-11-15 | Procedimiento para la preparacion de pirimidinas halogena- das. |
| SE1594067A SE332989B (is") | 1967-04-20 | 1967-11-20 | |
| BE707203D BE707203A (is") | 1967-04-20 | 1967-11-28 | |
| NO17076367A NO121341B (is") | 1967-04-20 | 1967-11-30 | |
| AT1093967A AT281034B (de) | 1967-04-20 | 1967-12-04 | Verfahren zur Herstellung von Halogenpyrimidinen |
| FR131195A FR1546395A (fr) | 1967-04-20 | 1967-12-06 | Procédé de fabrication d'halogénopyrimidines |
| US61469A US3682916A (en) | 1967-04-20 | 1970-08-05 | Process for the production of halopyrimidines |
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 (2)
| Publication Number | Publication Date |
|---|---|
| DE1670854A1 DE1670854A1 (de) | 1971-03-18 |
| DE1670854B2 true DE1670854B2 (de) | 1977-04-28 |
Family
ID=7105251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967F0052193 Granted DE1670854B2 (de) | 1967-04-20 | 1967-04-20 | Verfahren zur herstellung von 2,4,6- trichlorpyrimidinen |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT281034B (is") |
| BE (1) | BE707203A (is") |
| CH (1) | CH503034A (is") |
| DE (1) | DE1670854B2 (is") |
| DK (1) | DK117492B (is") |
| ES (1) | ES347176A1 (is") |
| GB (1) | GB1156408A (is") |
| NL (1) | NL6715452A (is") |
| NO (1) | NO121341B (is") |
| SE (1) | SE332989B (is") |
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 (is") | 1971-03-01 |
| DE1670854A1 (de) | 1971-03-18 |
| CH503034A (de) | 1971-02-15 |
| DK117492B (da) | 1970-05-04 |
| ES347176A1 (es) | 1969-01-16 |
| BE707203A (is") | 1968-05-28 |
| NO121341B (is") | 1971-02-15 |
| GB1156408A (en) | 1969-06-25 |
| AT281034B (de) | 1970-05-11 |
| NL6715452A (is") | 1968-10-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |