CH627456A5 - Process for preparing 3-phenyl-4,6-dichloropyridazine - Google Patents
Process for preparing 3-phenyl-4,6-dichloropyridazine Download PDFInfo
- Publication number
- CH627456A5 CH627456A5 CH48877A CH48877A CH627456A5 CH 627456 A5 CH627456 A5 CH 627456A5 CH 48877 A CH48877 A CH 48877A CH 48877 A CH48877 A CH 48877A CH 627456 A5 CH627456 A5 CH 627456A5
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- dichloropyridazine
- chlorination
- phosphorus oxychloride
- chlorine
- Prior art date
Links
- PPYSGGOWIZSMJL-UHFFFAOYSA-N 4,6-dichloro-3-phenylpyridazine Chemical compound N1=NC(Cl)=CC(Cl)=C1C1=CC=CC=C1 PPYSGGOWIZSMJL-UHFFFAOYSA-N 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 40
- BUBRFWDEAVIFMV-UHFFFAOYSA-N 3-chloro-6-phenylpyridazine Chemical compound N1=NC(Cl)=CC=C1C1=CC=CC=C1 BUBRFWDEAVIFMV-UHFFFAOYSA-N 0.000 claims description 17
- 238000005660 chlorination reaction Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- BVPVWXGCEPJZRZ-UHFFFAOYSA-N 3,4,5-trichloro-6-phenylpyridazine Chemical compound ClC1=C(Cl)C(Cl)=NN=C1C1=CC=CC=C1 BVPVWXGCEPJZRZ-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910019213 POCl3 Inorganic materials 0.000 claims description 7
- DGKIYVQEFBTNMF-UHFFFAOYSA-N 3,4-dichloro-6-phenylpyridazine Chemical compound N1=C(Cl)C(Cl)=CC(C=2C=CC=CC=2)=N1 DGKIYVQEFBTNMF-UHFFFAOYSA-N 0.000 claims description 6
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- TVKFDBOFBKXOQT-UHFFFAOYSA-N 5-phenyl-1h-pyridazin-6-one Chemical compound O=C1NN=CC=C1C1=CC=CC=C1 TVKFDBOFBKXOQT-UHFFFAOYSA-N 0.000 claims description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- LUMLZKVIXLWTCI-NSCUHMNNSA-N (e)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C=O LUMLZKVIXLWTCI-NSCUHMNNSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/12—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762612752 DE2612752A1 (de) | 1976-03-25 | 1976-03-25 | Verfahren zur herstellung von 3-phenyl-4,6-dichlorpyridazin |
| AT230276A AT340942B (de) | 1976-03-25 | 1976-03-30 | Verfahren zur herstellung von 3-phenyl-4,6-dichlorpyridazin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH627456A5 true CH627456A5 (en) | 1982-01-15 |
Family
ID=25598158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH48877A CH627456A5 (en) | 1976-03-25 | 1977-01-14 | Process for preparing 3-phenyl-4,6-dichloropyridazine |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS52118482A (OSRAM) |
| AT (1) | AT340942B (OSRAM) |
| CH (1) | CH627456A5 (OSRAM) |
| DE (1) | DE2612752A1 (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5916420U (ja) * | 1982-07-26 | 1984-01-31 | 丸江産業株式会社 | カバンの取手装置 |
-
1976
- 1976-03-25 DE DE19762612752 patent/DE2612752A1/de not_active Withdrawn
- 1976-03-30 AT AT230276A patent/AT340942B/de not_active IP Right Cessation
-
1977
- 1977-01-14 CH CH48877A patent/CH627456A5/de not_active IP Right Cessation
- 1977-03-24 JP JP3167477A patent/JPS52118482A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2612752A1 (de) | 1977-10-06 |
| ATA230276A (de) | 1977-05-15 |
| JPS52118482A (en) | 1977-10-04 |
| AT340942B (de) | 1978-01-10 |
| JPS56427B2 (OSRAM) | 1981-01-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |