IE39088L - 1,3,4-oxadiazolin-2-one derivatives. - Google Patents
1,3,4-oxadiazolin-2-one derivatives.Info
- Publication number
- IE39088L IE39088L IE740599A IE59974A IE39088L IE 39088 L IE39088 L IE 39088L IE 740599 A IE740599 A IE 740599A IE 59974 A IE59974 A IE 59974A IE 39088 L IE39088 L IE 39088L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- general formula
- oxadiazolin
- march
- isopropyl
- Prior art date
Links
- XLUWNAXYGUQQJL-UHFFFAOYSA-N 2h-1,3,4-oxadiazol-5-one Chemical class O=C1OCN=N1 XLUWNAXYGUQQJL-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 2
- 238000006665 Bamberger reaction Methods 0.000 abstract 2
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 abstract 1
- OAAHNXOPOHSZIJ-UHFFFAOYSA-N 2-propan-2-yl-2h-1,3,4-oxadiazol-5-one Chemical compound CC(C)C1OC(=O)N=N1 OAAHNXOPOHSZIJ-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- JKNSMBZZZFGYCB-UHFFFAOYSA-N 4,5-dihydrooxadiazole Chemical class C1CN=NO1 JKNSMBZZZFGYCB-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- -1 hydroxylamino group Chemical group 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 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)
Abstract
1416289 Process for 3-phenyl oxadiazoline derivatives RHONE-POULENC SA 20 March 1974 [22 March 1973] 12458/74 Heading C2C Oxadiazoline derivatives of general formula where R is a C 1-4 straight or branched alkyl radical, are obtained by reducing the nitro group in a compound of general formula to a hydroxylamino group by methods known per se which do not affect the rest of the molecule and converting this novel product of general formula by means of the Bamberger rearrangement to an aminophenol of general formula and converting the latter by methods known per se to the desired product without affecting the rest of the molecule. The reduction step is preferably effected with hydrogen in the presence of a Pd on carbon catalyst at 15-25‹ C. at atmospheric pressure. The Bamberger rearrangement may be performed by treatment with a strong inorganic acid such as H 2 SO 4 at a temperature below 25‹ C. The conversion of the amino phenol of Formula IV into product of Formula I is preferably achieved via the corresponding diazonium salt. The compounds of Formula I may be converted to compounds of formula by reacting with an alkyl halide of formula R<SP>1</SP> 1 X where R<SP>1</SP> 1 is C 1-4 alkyl. 5 - (t - Butyl)- and 5 - isopropyl - 3 - (2 - nitro- 4 - chlorophenyl) - 1,3,4 - oxadiazolin - 2 - one are produced by condensing 2,5-dichloronitrobenzene with 5-(t-butyl)- or 5-isopropyl-1,3,4- oxadiazolin-2-one respectively.
[GB1416289A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7310291A FR2222378B1 (en) | 1973-03-22 | 1973-03-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE39088L true IE39088L (en) | 1974-09-22 |
| IE39088B1 IE39088B1 (en) | 1978-08-02 |
Family
ID=9116690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE599/74A IE39088B1 (en) | 1973-03-22 | 1974-03-20 | Process for the preparation of oxadiazoline derivatives |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5833230B2 (en) |
| AT (1) | AT334369B (en) |
| BE (1) | BE812654A (en) |
| CA (1) | CA1026344A (en) |
| CH (1) | CH591460A5 (en) |
| DE (1) | DE2413938A1 (en) |
| FR (1) | FR2222378B1 (en) |
| GB (1) | GB1416289A (en) |
| HU (1) | HU168296B (en) |
| IE (1) | IE39088B1 (en) |
| IL (1) | IL44467A (en) |
| IT (1) | IT1003804B (en) |
| NL (1) | NL181195C (en) |
| SU (1) | SU635870A3 (en) |
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 (en) * | 1968-01-30 | 1969-03-14 | ||
| FR2141442B1 (en) * | 1971-06-02 | 1973-06-29 | Rhone Poulenc Sa | |
| FR2141443B1 (en) * | 1971-06-02 | 1973-06-29 | Rhone Poulenc Sa | |
| BE788612A (en) * | 1971-09-09 | 1973-03-08 | Rhone Poulenc Sa | NEW HERBICIDES |
-
1973
- 1973-03-22 FR FR7310291A patent/FR2222378B1/fr not_active Expired
-
1974
- 1974-03-14 NL NLAANVRAGE7403446,A patent/NL181195C/en not_active IP Right Cessation
- 1974-03-20 HU HURO774A patent/HU168296B/hu unknown
- 1974-03-20 IE IE599/74A patent/IE39088B1/en unknown
- 1974-03-20 GB GB1245874A patent/GB1416289A/en not_active Expired
- 1974-03-20 JP JP49031078A patent/JPS5833230B2/en not_active Expired
- 1974-03-20 CA CA195,468A patent/CA1026344A/en not_active Expired
- 1974-03-21 IT IT49393/74A patent/IT1003804B/en active
- 1974-03-21 BE BE142298A patent/BE812654A/en not_active IP Right Cessation
- 1974-03-21 CH CH393974A patent/CH591460A5/xx not_active IP Right Cessation
- 1974-03-21 IL IL44467A patent/IL44467A/en unknown
- 1974-03-21 SU SU742007934A patent/SU635870A3/en active
- 1974-03-22 AT AT239774A patent/AT334369B/en not_active IP Right Cessation
- 1974-03-22 DE DE2413938A patent/DE2413938A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2222378A1 (en) | 1974-10-18 |
| CA1026344A (en) | 1978-02-14 |
| GB1416289A (en) | 1975-12-03 |
| BE812654A (en) | 1974-09-23 |
| IT1003804B (en) | 1976-06-10 |
| AT334369B (en) | 1976-01-10 |
| JPS5833230B2 (en) | 1983-07-18 |
| JPS49126678A (en) | 1974-12-04 |
| NL181195C (en) | 1987-07-01 |
| DE2413938A1 (en) | 1974-09-26 |
| DE2413938C2 (en) | 1987-12-03 |
| CH591460A5 (en) | 1977-09-15 |
| IL44467A0 (en) | 1974-06-30 |
| NL181195B (en) | 1987-02-02 |
| IE39088B1 (en) | 1978-08-02 |
| IL44467A (en) | 1977-04-29 |
| ATA239774A (en) | 1976-05-15 |
| NL7403446A (en) | 1974-09-24 |
| HU168296B (en) | 1976-03-28 |
| FR2222378B1 (en) | 1976-11-05 |
| SU635870A3 (en) | 1978-11-30 |
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