JPS6254102B2 - - Google Patents
Info
- Publication number
- JPS6254102B2 JPS6254102B2 JP52157364A JP15736477A JPS6254102B2 JP S6254102 B2 JPS6254102 B2 JP S6254102B2 JP 52157364 A JP52157364 A JP 52157364A JP 15736477 A JP15736477 A JP 15736477A JP S6254102 B2 JPS6254102 B2 JP S6254102B2
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- distilled
- water
- singlet
- proton
- 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
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 229930040373 Paraformaldehyde Natural products 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 229920002866 paraformaldehyde Polymers 0.000 description 8
- -1 5-methyl-3-phenylthiazolidin-4-one Chemical compound 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- KMSNYNIWEORQDJ-UHFFFAOYSA-N Dihydro-2(3H)-thiophenone Chemical compound O=C1CCCS1 KMSNYNIWEORQDJ-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- QYQHWRYESWRIJQ-UHFFFAOYSA-N 2-benzyl-1,3-thiazolidin-4-one Chemical compound N1C(=O)CSC1CC1=CC=CC=C1 QYQHWRYESWRIJQ-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- COKNNGZXSAVGOU-UHFFFAOYSA-N 3-methyl-1,3-thiazolidin-4-one Chemical compound CN1CSCC1=O COKNNGZXSAVGOU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002036 chloroform fraction Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15736477A JPS5492955A (en) | 1977-12-28 | 1977-12-28 | Heterocyclic compound and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15736477A JPS5492955A (en) | 1977-12-28 | 1977-12-28 | Heterocyclic compound and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5492955A JPS5492955A (en) | 1979-07-23 |
| JPS6254102B2 true JPS6254102B2 (fr) | 1987-11-13 |
Family
ID=15648035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15736477A Granted JPS5492955A (en) | 1977-12-28 | 1977-12-28 | Heterocyclic compound and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5492955A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4664694A (en) * | 1985-04-24 | 1987-05-12 | Uniroyal Chemical Company, Inc. | Substituted thiazolidinones useful as plant growth regulators |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2226242A1 (de) * | 1972-05-30 | 1973-12-06 | Bayer Ag | 3-alkyl-4-aryliminothiazolidine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1977
- 1977-12-28 JP JP15736477A patent/JPS5492955A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2226242A1 (de) * | 1972-05-30 | 1973-12-06 | Bayer Ag | 3-alkyl-4-aryliminothiazolidine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5492955A (en) | 1979-07-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI88617B (fi) | Trans-6-/2-(3- eller 4-karboxamido-substituerad pyrrol-1-yl)alkyl/-4-hydroxipyran-2-oner saosom kolesterolsyntesinhibitorer | |
| JPH0331715B2 (fr) | ||
| SK147897A3 (en) | Azacycloalcane derivatives, preparation thereof and their applications in therapy | |
| US4102886A (en) | Process for the preparation of benzo(a)quinolizidine derivatives | |
| JPS6159313B2 (fr) | ||
| SU581869A3 (ru) | Способ получени производных ксантена | |
| SU598557A3 (ru) | Способ получени производных 1-фенокси-3-аминопропан-2-ола или их солей | |
| JPS6254102B2 (fr) | ||
| US4874773A (en) | 3-Aminocarbonyl-1,4-dihydropyridine-5-carboxylic acid compounds, and pharmaceutical composition containing the same | |
| JPS6212776A (ja) | ロ−ダニン誘導体 | |
| SU428602A3 (ru) | Способ получения основпозамещенных производных 1 | |
| KR960012371B1 (ko) | 신규 5-메톡시 알킬 암모늄 테트라히드로푸란 및 테트라히드로티오펜 | |
| SU670216A3 (ru) | Способ получени производных оксима или их солей | |
| CA1182116A (fr) | Methode de preparation de 5,6,7,7atetrahydro-4h- thieno-3,2-c| pyridin-2-one | |
| EP0511031A1 (fr) | Dérivés d'aryl-3 oxazolidinone, leur procédé de préparation et leur application en thérapeutique | |
| FI62531C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbart 3-yan-n-(n n-dimetylamino-propyl)-iminodibensyl och syraadd itonssalter daerav | |
| JP2778366B2 (ja) | ６−フルオロベンズイソチアゾール類の製造方法およびそのための中間体 | |
| SU576935A3 (ru) | Способ получени производных тетразолилуксусной кислоты или ее эфиров, или их солей | |
| CA1121823A (fr) | Procede d'obtention de derives d'acides 1-pyrrole et 1-pyrrolidine-carboxyliques | |
| KR840001034B1 (ko) | 디하이드로니코틴산 유도체의 제조방법 | |
| JP4452969B2 (ja) | インドール化合物、その製造方法および用途 | |
| JPH0534351B2 (fr) | ||
| SU549075A3 (ru) | Способ получени производных флуоренона или их солей | |
| JPS59184182A (ja) | ３−ベンゾイルチオ−４、５α−エポキシ−７α−〔１（Ｒ）−ヒドロキシ−１−メチルベンチル〕−６−メトキシ−１７−メチル−６、１４−エンド−エタノモルヒナン | |
| JPS6348273B2 (fr) |