KR840001153A - 5,6-디하이드로-2-메틸-n-페닐-1,4-옥사티인-3-카복사미드 및 그 중간체의 제조장법 - Google Patents
5,6-디하이드로-2-메틸-n-페닐-1,4-옥사티인-3-카복사미드 및 그 중간체의 제조장법 Download PDFInfo
- Publication number
- KR840001153A KR840001153A KR1019820003584A KR820003584A KR840001153A KR 840001153 A KR840001153 A KR 840001153A KR 1019820003584 A KR1019820003584 A KR 1019820003584A KR 820003584 A KR820003584 A KR 820003584A KR 840001153 A KR840001153 A KR 840001153A
- Authority
- KR
- South Korea
- Prior art keywords
- hydroxyethyl
- disulfide
- reaction mixture
- reaction
- process according
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 7
- KYNFOMQIXZUKRK-UHFFFAOYSA-N 2,2'-dithiodiethanol Chemical compound OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 claims 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 6
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims 6
- 239000011541 reaction mixture Substances 0.000 claims 5
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 3
- CSQOAEIMKOPVBK-UHFFFAOYSA-N 2-(2-hydroxyethylsulfanyl)-3-oxo-n-phenylbutanamide Chemical compound OCCSC(C(=O)C)C(=O)NC1=CC=CC=C1 CSQOAEIMKOPVBK-UHFFFAOYSA-N 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- XHZQXECGWRSNJO-UHFFFAOYSA-N C(COS(=O)OS(=O)OCCO)O Chemical compound C(COS(=O)OS(=O)OCCO)O XHZQXECGWRSNJO-UHFFFAOYSA-N 0.000 claims 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- 디-(2-하이드록시에틸)디설파이드를 아세토아세트아닐리드와 반응시켜 중간체 2-[(2-하이드록시틸)티오]-3-옥소-N-페닐-부탄아미드를 제조하고, 이를 고리화반응시켜 5,6-디하이드로-2-메틸-N-페닐-1,4-옥사티인-3-카복사미드를 제조하는 방법.
- 디-(2-하이드록시에틸)디설파이드를 이온 형태의 아세토아세트아닐리드와 반응시켜 2-[(2-하이드록시에틸)티오]-3-옥소-N-페닐부탄아미드를 제조하는 방법.
- 제2항에 있어서, 디-(2-하이드록시에틸)디설파이드가 반응 혼합물에 첨가되기 전에 미리 제조되는 제조방법.
- 제2항에 있어서, 디-(2-하이드록시에틸)디설파이드가 반응혼합물 자체내에서 제조되는 제조방법.
- 제4항에 있어서, 디-(2-하이드록시에틸)디설파이드가 2-머캅토에탄올을 첨가하고 이를 과산화수소 또는 공기로 산화시켜 자체내에서 제조되는 제조방법.
- 제2항에 있어서, 아세토아세트아닐리드가 수용성 및/또는 알콜성 염기중에 용해되는 제조방법.
- 제2항에 있어서, 반응혼합물이 25 내지 50℃ 온도 범위로 유지되는 제조방법.
- 제2항에 있어서, 염기를 과잉량 사용하고 또 부산물 2-머캅토에탄올을 과산화수소 또는 공기로서 자체내에서 디-(2-하이드록시-에틸)디설파이트로 산화시켜줌으로서 반응평형을 목적생성물 방향으로 이동시킨 제조방법.
- 제2항에 있어서, 아세토아세트아닐리드/염기의 몰비율이 약 1/1이고, 수득한 베타-디케톤에에이트 염기의 농도가 200 내지 60% 범위이고, 디설파이드/아세토아세트니트릴의 몰비율이 1.5/1이며 또 2-머캅토에탄올의 이론 생성량을 기준으로 0 내지 15% 과잉의 30 내지 50%과산화수소가 첨가되는 제조방법.
- 제2항에 있어서, 반응혼합물이 2-[(2-하이드록시에틸)티오]-3-옥소-N-페닐부탄아미드 생성물을 분리하기 위하여 반응종료후에 산성화시키고 또 유기용매로 추출한 수용액이며 또 수용성상에 잔유하는 과잉의 디-(2-하이드록시에틸)디설파이드가 재순환되는 제조방법.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000383592A CA1166262A (en) | 1981-08-11 | 1981-08-11 | Synthesis of intermediate for the manufacture of 5,6- dihydro-2-methyl-n-phenyl-1,4-oxathiin-3-carboxamide |
| CA383,592 | 1981-08-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840001153A true KR840001153A (ko) | 1984-03-28 |
| KR860000102B1 KR860000102B1 (ko) | 1986-02-19 |
Family
ID=4120659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8203584A KR860000102B1 (ko) | 1981-08-11 | 1982-08-10 | 5, 6-디하이드로-2-메틸-n-페닐-1, 4-옥사티인-3-카복사미드 및 그 중간체의 제조방법 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4359579A (ko) |
| EP (1) | EP0072106B1 (ko) |
| JP (1) | JPS6052153B2 (ko) |
| KR (1) | KR860000102B1 (ko) |
| AU (1) | AU550553B2 (ko) |
| BG (1) | BG37076A3 (ko) |
| BR (1) | BR8204245A (ko) |
| CA (1) | CA1166262A (ko) |
| DD (1) | DD202708A5 (ko) |
| DE (1) | DE3266930D1 (ko) |
| ES (1) | ES514886A0 (ko) |
| GB (1) | GB2103606B (ko) |
| GR (1) | GR77221B (ko) |
| HU (1) | HU187781B (ko) |
| IL (1) | IL66369A0 (ko) |
| PL (1) | PL237854A1 (ko) |
| RO (1) | RO85553B1 (ko) |
| SU (1) | SU1155156A3 (ko) |
| TR (1) | TR21590A (ko) |
| YU (1) | YU173682A (ko) |
| ZA (1) | ZA824846B (ko) |
| ZW (1) | ZW14082A1 (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5268389A (en) | 1989-10-16 | 1993-12-07 | Uniroyal Chemical Company, Inc. | Thiocarboxylate ester compounds compositions containing the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3393202A (en) * | 1965-04-26 | 1968-07-16 | Uniroyal Inc | 2, 3-dihydro-5-carboxamido-6-methyl-1, 4-oxathins and method of making same |
| US3399214A (en) * | 1965-11-05 | 1968-08-27 | Uniroyal Inc | Oxides of carboxamido oxathiins |
| US3728357A (en) * | 1970-09-08 | 1973-04-17 | Uniroyal Inc | 2-(substituted-methyl)-5,6-dihydro-1,4-oxathiin-3-carboxamides |
| DE2164805A1 (de) * | 1970-12-29 | 1972-07-13 | Fuji Photo Film Co. Ltd., Ashigara-Kamigun, Kanagawa (Japan) | Verfahren zur Herstellung einer eine Thiogruppe enthaltenden Verbindung |
| CA1036167A (en) * | 1977-05-06 | 1978-08-08 | Wha S. Lee | Process for preparing 5,6-dihydro-2-methyl-1,4-oxathiin derivatives |
| US4230871A (en) * | 1979-04-02 | 1980-10-28 | Lee Wha S | Process for preparing 5,6-dihydro-2-methyl-1,4-oxathiin derivatives |
-
1981
- 1981-08-11 CA CA000383592A patent/CA1166262A/en not_active Expired
- 1981-08-24 US US06/295,394 patent/US4359579A/en not_active Expired - Lifetime
-
1982
- 1982-07-06 AU AU85629/82A patent/AU550553B2/en not_active Ceased
- 1982-07-07 ZA ZA824846A patent/ZA824846B/xx unknown
- 1982-07-12 EP EP82303650A patent/EP0072106B1/en not_active Expired
- 1982-07-12 DE DE8282303650T patent/DE3266930D1/de not_active Expired
- 1982-07-12 GB GB08220156A patent/GB2103606B/en not_active Expired
- 1982-07-13 ZW ZW140/82A patent/ZW14082A1/xx unknown
- 1982-07-21 BR BR8204245A patent/BR8204245A/pt unknown
- 1982-07-21 IL IL66369A patent/IL66369A0/xx not_active IP Right Cessation
- 1982-08-05 TR TR21590A patent/TR21590A/xx unknown
- 1982-08-09 GR GR68985A patent/GR77221B/el unknown
- 1982-08-09 BG BG057688A patent/BG37076A3/xx unknown
- 1982-08-09 DD DD82242363A patent/DD202708A5/de unknown
- 1982-08-09 RO RO108416A patent/RO85553B1/ro unknown
- 1982-08-10 YU YU01736/82A patent/YU173682A/xx unknown
- 1982-08-10 PL PL23785482A patent/PL237854A1/xx unknown
- 1982-08-10 HU HU822582A patent/HU187781B/hu unknown
- 1982-08-10 ES ES514886A patent/ES514886A0/es active Granted
- 1982-08-10 SU SU823476700A patent/SU1155156A3/ru active
- 1982-08-10 JP JP57139099A patent/JPS6052153B2/ja not_active Expired
- 1982-08-10 KR KR8203584A patent/KR860000102B1/ko active
Also Published As
| Publication number | Publication date |
|---|---|
| SU1155156A3 (ru) | 1985-05-07 |
| PL237854A1 (en) | 1983-04-11 |
| ZW14082A1 (en) | 1982-10-06 |
| YU173682A (en) | 1984-12-31 |
| DE3266930D1 (en) | 1985-11-21 |
| EP0072106A1 (en) | 1983-02-16 |
| ES8400424A1 (es) | 1983-11-01 |
| ZA824846B (en) | 1983-04-27 |
| GR77221B (ko) | 1984-09-11 |
| DD202708A5 (de) | 1983-09-28 |
| CA1166262A (en) | 1984-04-24 |
| AU8562982A (en) | 1983-02-17 |
| RO85553A2 (ro) | 1985-02-25 |
| JPS5838280A (ja) | 1983-03-05 |
| BR8204245A (pt) | 1983-07-12 |
| JPS6052153B2 (ja) | 1985-11-18 |
| GB2103606B (en) | 1985-09-18 |
| KR860000102B1 (ko) | 1986-02-19 |
| AU550553B2 (en) | 1986-03-27 |
| ES514886A0 (es) | 1983-11-01 |
| GB2103606A (en) | 1983-02-23 |
| TR21590A (tr) | 1984-11-12 |
| HU187781B (en) | 1986-02-28 |
| US4359579A (en) | 1982-11-16 |
| IL66369A0 (en) | 1982-11-30 |
| RO85553B1 (ro) | 1985-02-28 |
| BG37076A3 (en) | 1985-03-15 |
| EP0072106B1 (en) | 1985-10-16 |
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