DE2220256C3 - N-(o- bzw. p-nitrobenzoyl)-sulfoximine, verfahren zu ihrer herstellung und verwendung derselben - Google Patents
N-(o- bzw. p-nitrobenzoyl)-sulfoximine, verfahren zu ihrer herstellung und verwendung derselbenInfo
- Publication number
- DE2220256C3 DE2220256C3 DE19722220256 DE2220256A DE2220256C3 DE 2220256 C3 DE2220256 C3 DE 2220256C3 DE 19722220256 DE19722220256 DE 19722220256 DE 2220256 A DE2220256 A DE 2220256A DE 2220256 C3 DE2220256 C3 DE 2220256C3
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- sulfoximine
- nitrobenzoyl
- mol
- acid
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 5
- YQYGPGKTNQNXMH-UHFFFAOYSA-N 4-nitroacetophenone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1 YQYGPGKTNQNXMH-UHFFFAOYSA-N 0.000 title 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 15
- 125000005555 sulfoximide group Chemical group 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000003462 sulfoxides Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- OZUBFIYPXMVSPY-UHFFFAOYSA-N 4-nitro-N-[oxo(diphenyl)-lambda6-sulfanylidene]benzamide Chemical compound [N+](=O)([O-])C1=CC=C(C(=O)N=S(=O)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 OZUBFIYPXMVSPY-UHFFFAOYSA-N 0.000 description 4
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 N-substituted sulfoximines Chemical class 0.000 description 3
- DGCQHHXNQRYLBM-UHFFFAOYSA-N [(4-nitrobenzoyl)amino] acetate Chemical compound CC(=O)ONC(=O)C1=CC=C([N+]([O-])=O)C=C1 DGCQHHXNQRYLBM-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- KNPJTNDEHOFWKA-UHFFFAOYSA-N imino-oxo-diphenyl-$l^{6}-sulfane Chemical compound C=1C=CC=CC=1S(=O)(=N)C1=CC=CC=C1 KNPJTNDEHOFWKA-UHFFFAOYSA-N 0.000 description 2
- VSQUNYJOMUFPIT-UHFFFAOYSA-N imino-oxo-diphenyl-$l^{6}-sulfane;hydrochloride Chemical group Cl.C=1C=CC=CC=1S(=O)(=N)C1=CC=CC=C1 VSQUNYJOMUFPIT-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- JXTGICXCHWMCPM-UHFFFAOYSA-N (methylsulfinyl)benzene Chemical compound CS(=O)C1=CC=CC=C1 JXTGICXCHWMCPM-UHFFFAOYSA-N 0.000 description 1
- LEDPSBGADKSDKI-UHFFFAOYSA-N 1-methoxy-4-(4-methoxyphenyl)sulfinylbenzene Chemical compound C1=CC(OC)=CC=C1S(=O)C1=CC=C(OC)C=C1 LEDPSBGADKSDKI-UHFFFAOYSA-N 0.000 description 1
- AXYZTWMGRALTCR-UHFFFAOYSA-N COC1=CC=C(S(=N)=O)C=C1 Chemical compound COC1=CC=C(S(=N)=O)C=C1 AXYZTWMGRALTCR-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- UBEAFRVHSDHHCI-UHFFFAOYSA-N [(2-nitrobenzoyl)amino] acetate Chemical compound CC(=O)ONC(=O)C1=CC=CC=C1[N+]([O-])=O UBEAFRVHSDHHCI-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- OBKGRRCDSDBSHK-UHFFFAOYSA-N [N+](=O)([O-])N=S(=O)C(C1=CC=CC=C1)=O Chemical class [N+](=O)([O-])N=S(=O)C(C1=CC=CC=C1)=O OBKGRRCDSDBSHK-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- OAVWFBZFERWKEP-UHFFFAOYSA-N n-(methyl-oxo-phenyl-$l^{6}-sulfanylidene)-4-nitrobenzamide Chemical compound C=1C=CC=CC=1S(=O)(C)=NC(=O)C1=CC=C([N+]([O-])=O)C=C1 OAVWFBZFERWKEP-UHFFFAOYSA-N 0.000 description 1
- TXZYNGWHYSAFLX-UHFFFAOYSA-N n-[dimethyl(oxo)-$l^{6}-sulfanylidene]-4-nitrobenzamide Chemical compound CS(C)(=O)=NC(=O)C1=CC=C([N+]([O-])=O)C=C1 TXZYNGWHYSAFLX-UHFFFAOYSA-N 0.000 description 1
- LGEVIFOJNNPCNI-UHFFFAOYSA-N n-hydroxy-2-nitrobenzamide Chemical class ONC(=O)C1=CC=CC=C1[N+]([O-])=O LGEVIFOJNNPCNI-UHFFFAOYSA-N 0.000 description 1
- 150000005440 nitrobenzoic acid derivatives Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722220256 DE2220256C3 (de) | 1972-04-25 | 1972-04-25 | N-(o- bzw. p-nitrobenzoyl)-sulfoximine, verfahren zu ihrer herstellung und verwendung derselben |
| AU54109/73A AU470030B2 (en) | 1972-04-25 | 1973-04-04 | Novel n-(ortho-and para-nitrobenzoyl) sulfosimine intermediates and process for their production |
| GB1716173A GB1394007A (en) | 1972-04-25 | 1973-04-10 | Sulphoximines |
| US35111273 US3868418A (en) | 1972-04-25 | 1973-04-13 | Novel N-(ortho- and para-nitrobenzoyl)-sulfoximine intermediates and process for their production |
| CA169,302A CA986954A (en) | 1972-04-25 | 1973-04-24 | N-(o- and p-nitrobenzoyl)-sulfoximines; process for their production and use thereof |
| JP4657573A JPS563864B2 (enExample) | 1972-04-25 | 1973-04-24 | |
| US50401374 US3919310A (en) | 1972-04-25 | 1974-09-09 | Preparation of free sulfoximines by hydrolysis of N-(ortho- and para-nitrobenzoyl)-sulfoximines |
| JP2725680A JPS55141464A (en) | 1972-04-25 | 1980-03-04 | Manufacture of sulfoxyimine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722220256 DE2220256C3 (de) | 1972-04-25 | 1972-04-25 | N-(o- bzw. p-nitrobenzoyl)-sulfoximine, verfahren zu ihrer herstellung und verwendung derselben |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2220256A1 DE2220256A1 (de) | 1973-11-08 |
| DE2220256B2 DE2220256B2 (de) | 1975-07-03 |
| DE2220256C3 true DE2220256C3 (de) | 1976-02-19 |
Family
ID=5843218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722220256 Expired DE2220256C3 (de) | 1972-04-25 | 1972-04-25 | N-(o- bzw. p-nitrobenzoyl)-sulfoximine, verfahren zu ihrer herstellung und verwendung derselben |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3868418A (enExample) |
| JP (2) | JPS563864B2 (enExample) |
| AU (1) | AU470030B2 (enExample) |
| CA (1) | CA986954A (enExample) |
| DE (1) | DE2220256C3 (enExample) |
| GB (1) | GB1394007A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4113738A (en) * | 1977-02-02 | 1978-09-12 | Polaroid Corporation | Conversion of N-tosylsulfoximides to sulfoximines |
| JPS5841381B2 (ja) * | 1978-01-19 | 1983-09-12 | ボルボ ビ−エム アクチ−ボラグ | 迅速カツプリング装置 |
| JPS57104331U (enExample) * | 1980-12-18 | 1982-06-26 | ||
| JPS5830899U (ja) * | 1981-08-26 | 1983-02-28 | 株式会社原子力代行 | フイルタ−ハウジングの配管離脱装置 |
| JPS60121388A (ja) * | 1983-11-14 | 1985-06-28 | ダイキン工業株式会社 | 耐蝕性の簡易着脱配管継手 |
| JPS60171081U (ja) * | 1984-04-17 | 1985-11-13 | ソニー株式会社 | 安定化電源回路 |
| JPH08128580A (ja) * | 1994-10-28 | 1996-05-21 | Niyuumach:Kk | 管継手 |
-
1972
- 1972-04-25 DE DE19722220256 patent/DE2220256C3/de not_active Expired
-
1973
- 1973-04-04 AU AU54109/73A patent/AU470030B2/en not_active Expired
- 1973-04-10 GB GB1716173A patent/GB1394007A/en not_active Expired
- 1973-04-13 US US35111273 patent/US3868418A/en not_active Expired - Lifetime
- 1973-04-24 CA CA169,302A patent/CA986954A/en not_active Expired
- 1973-04-24 JP JP4657573A patent/JPS563864B2/ja not_active Expired
-
1980
- 1980-03-04 JP JP2725680A patent/JPS55141464A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| Nichts Ermittelt * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU470030B2 (en) | 1976-03-04 |
| AU5410973A (en) | 1974-10-10 |
| JPS563864B2 (enExample) | 1981-01-27 |
| JPS55141464A (en) | 1980-11-05 |
| DE2220256B2 (de) | 1975-07-03 |
| JPS4947337A (enExample) | 1974-05-08 |
| US3868418A (en) | 1975-02-25 |
| DE2220256A1 (de) | 1973-11-08 |
| GB1394007A (en) | 1975-05-14 |
| JPS5638588B2 (enExample) | 1981-09-08 |
| CA986954A (en) | 1976-04-06 |
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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 | ||
| 8339 | Ceased/non-payment of the annual fee |