IL44467A - Process for the preparation of 5-alkyl-3-(2,4-dichloro-5-hydroxyphenyl)-1,3,4-oxadiazolin-2(3h)-ones and novel 5-alkyl-3-(4-chloro-2-hydroxyaminophenyl)1,3,4-oxadiazolin-2(3h)-ones - Google Patents
Process for the preparation of 5-alkyl-3-(2,4-dichloro-5-hydroxyphenyl)-1,3,4-oxadiazolin-2(3h)-ones and novel 5-alkyl-3-(4-chloro-2-hydroxyaminophenyl)1,3,4-oxadiazolin-2(3h)-onesInfo
- Publication number
- IL44467A IL44467A IL44467A IL4446774A IL44467A IL 44467 A IL44467 A IL 44467A IL 44467 A IL44467 A IL 44467A IL 4446774 A IL4446774 A IL 4446774A IL 44467 A IL44467 A IL 44467A
- Authority
- IL
- Israel
- Prior art keywords
- general formula
- preparation
- derivatives
- oxadiazolin
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- -1 hydroxylamino group Chemical group 0.000 claims description 8
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000002828 nitro derivatives Chemical class 0.000 claims description 7
- 239000001117 sulphuric acid Substances 0.000 claims description 7
- 235000011149 sulphuric acid Nutrition 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 150000002443 hydroxylamines Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000012954 diazonium Substances 0.000 claims description 4
- 238000006665 Bamberger reaction Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- JKNSMBZZZFGYCB-UHFFFAOYSA-N 4,5-dihydrooxadiazole Chemical class C1CN=NO1 JKNSMBZZZFGYCB-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000155 melt Substances 0.000 description 14
- RZQQXRVPPOOCQR-UHFFFAOYSA-N 2,3-dihydro-1,3,4-oxadiazole Chemical class C1NN=CO1 RZQQXRVPPOOCQR-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 description 2
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WAUYWJOSIPLLSJ-UHFFFAOYSA-N 2-tert-butyl-2h-1,3,4-oxadiazol-5-one Chemical compound CC(C)(C)C1OC(=O)N=N1 WAUYWJOSIPLLSJ-UHFFFAOYSA-N 0.000 description 1
- IWSZZPNGYDFMMB-UHFFFAOYSA-N 3-(2,4-dichloro-5-propan-2-yloxyphenyl)-5-propan-2-yl-1,3,4-oxadiazol-2-one Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)C)=O)=C1Cl IWSZZPNGYDFMMB-UHFFFAOYSA-N 0.000 description 1
- GYXJAQUVWZJHGW-UHFFFAOYSA-N 3-(2-amino-4-chloro-5-hydroxyphenyl)-5-propan-2-yl-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(C(C)C)=NN1C1=CC(O)=C(Cl)C=C1N GYXJAQUVWZJHGW-UHFFFAOYSA-N 0.000 description 1
- OVWATYVJPKMCKY-UHFFFAOYSA-N 3-(2-amino-4-chloro-5-hydroxyphenyl)-5-tert-butyl-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(C(C)(C)C)=NN1C1=CC(O)=C(Cl)C=C1N OVWATYVJPKMCKY-UHFFFAOYSA-N 0.000 description 1
- SAXZXJDWFASLBE-UHFFFAOYSA-N 3-(4-chloro-2-nitrophenyl)-5-propan-2-yl-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(C(C)C)=NN1C1=CC=C(Cl)C=C1[N+]([O-])=O SAXZXJDWFASLBE-UHFFFAOYSA-N 0.000 description 1
- VYZIEJGBCSOXBK-UHFFFAOYSA-N 3-[4-chloro-2-(hydroxyamino)phenyl]-5-propan-2-yl-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(C(C)C)=NN1C1=CC=C(Cl)C=C1NO VYZIEJGBCSOXBK-UHFFFAOYSA-N 0.000 description 1
- ROPLUFUHDKBQPY-UHFFFAOYSA-N 5-tert-butyl-3-(4-chloro-2-nitrophenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(C(C)(C)C)=NN1C1=CC=C(Cl)C=C1[N+]([O-])=O ROPLUFUHDKBQPY-UHFFFAOYSA-N 0.000 description 1
- 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- MXJDHESCSJVNQP-UHFFFAOYSA-N [Na].CC#N Chemical compound [Na].CC#N MXJDHESCSJVNQP-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7310291A FR2222378B1 (enrdf_load_stackoverflow) | 1973-03-22 | 1973-03-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44467A0 IL44467A0 (en) | 1974-06-30 |
| IL44467A true IL44467A (en) | 1977-04-29 |
Family
ID=9116690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44467A IL44467A (en) | 1973-03-22 | 1974-03-21 | Process for the preparation of 5-alkyl-3-(2,4-dichloro-5-hydroxyphenyl)-1,3,4-oxadiazolin-2(3h)-ones and novel 5-alkyl-3-(4-chloro-2-hydroxyaminophenyl)1,3,4-oxadiazolin-2(3h)-ones |
Country Status (14)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138404A (en) | 1973-03-22 | 1979-02-06 | Rhone-Poulenc S.A. | Process for the preparation of oxadiazolines |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3535382A (en) * | 1967-11-02 | 1970-10-20 | Cpc International Inc | Amino phenol production |
| FR1559841A (enrdf_load_stackoverflow) * | 1968-01-30 | 1969-03-14 | ||
| FR2141443B1 (enrdf_load_stackoverflow) * | 1971-06-02 | 1973-06-29 | Rhone Poulenc Sa | |
| FR2141442B1 (enrdf_load_stackoverflow) * | 1971-06-02 | 1973-06-29 | Rhone Poulenc Sa | |
| BE788612A (fr) * | 1971-09-09 | 1973-03-08 | Rhone Poulenc Sa | Nouveaux herbicides |
-
1973
- 1973-03-22 FR FR7310291A patent/FR2222378B1/fr not_active Expired
-
1974
- 1974-03-14 NL NLAANVRAGE7403446,A patent/NL181195C/xx not_active IP Right Cessation
- 1974-03-20 GB GB1245874A patent/GB1416289A/en not_active Expired
- 1974-03-20 CA CA195,468A patent/CA1026344A/en not_active Expired
- 1974-03-20 HU HURO774A patent/HU168296B/hu unknown
- 1974-03-20 JP JP49031078A patent/JPS5833230B2/ja not_active Expired
- 1974-03-20 IE IE599/74A patent/IE39088B1/xx unknown
- 1974-03-21 BE BE142298A patent/BE812654A/xx not_active IP Right Cessation
- 1974-03-21 SU SU742007934A patent/SU635870A3/ru active
- 1974-03-21 CH CH393974A patent/CH591460A5/xx not_active IP Right Cessation
- 1974-03-21 IT IT49393/74A patent/IT1003804B/it active
- 1974-03-21 IL IL44467A patent/IL44467A/en unknown
- 1974-03-22 AT AT239774A patent/AT334369B/de not_active IP Right Cessation
- 1974-03-22 DE DE2413938A patent/DE2413938A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH591460A5 (enrdf_load_stackoverflow) | 1977-09-15 |
| HU168296B (enrdf_load_stackoverflow) | 1976-03-28 |
| FR2222378A1 (enrdf_load_stackoverflow) | 1974-10-18 |
| DE2413938C2 (enrdf_load_stackoverflow) | 1987-12-03 |
| IE39088L (en) | 1974-09-22 |
| DE2413938A1 (de) | 1974-09-26 |
| BE812654A (fr) | 1974-09-23 |
| NL181195C (nl) | 1987-07-01 |
| GB1416289A (en) | 1975-12-03 |
| SU635870A3 (ru) | 1978-11-30 |
| IE39088B1 (en) | 1978-08-02 |
| ATA239774A (de) | 1976-05-15 |
| IT1003804B (it) | 1976-06-10 |
| AT334369B (de) | 1976-01-10 |
| JPS49126678A (enrdf_load_stackoverflow) | 1974-12-04 |
| CA1026344A (en) | 1978-02-14 |
| JPS5833230B2 (ja) | 1983-07-18 |
| IL44467A0 (en) | 1974-06-30 |
| FR2222378B1 (enrdf_load_stackoverflow) | 1976-11-05 |
| NL7403446A (enrdf_load_stackoverflow) | 1974-09-24 |
| NL181195B (nl) | 1987-02-02 |
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