JPS645592B2 - - Google Patents
Info
- Publication number
- JPS645592B2 JPS645592B2 JP15807681A JP15807681A JPS645592B2 JP S645592 B2 JPS645592 B2 JP S645592B2 JP 15807681 A JP15807681 A JP 15807681A JP 15807681 A JP15807681 A JP 15807681A JP S645592 B2 JPS645592 B2 JP S645592B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- mixture
- carbon atoms
- formula
- added
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- KDBUUJSOUXNTOE-UHFFFAOYSA-N 2-bromopropanediamide Chemical compound NC(=O)C(Br)C(N)=O KDBUUJSOUXNTOE-UHFFFAOYSA-N 0.000 claims description 16
- -1 cyanoformate ester Chemical class 0.000 claims description 16
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 15
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 15
- 239000001119 stannous chloride Substances 0.000 claims description 15
- 235000011150 stannous chloride Nutrition 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- TUZVMPXGFZSNBG-UHFFFAOYSA-N 3-aminopyrrole-2,5-dione Chemical compound NC1=CC(=O)NC1=O TUZVMPXGFZSNBG-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000000203 mixture Substances 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- MSMGXWFHBSCQFB-UHFFFAOYSA-N ethyl cyanoformate Chemical compound CCOC(=O)C#N MSMGXWFHBSCQFB-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QTQZTRTXGIDTMP-UHFFFAOYSA-N 2-bromo-N,N'-dimethylpropanediamide Chemical compound CNC(C(C(=O)NC)Br)=O QTQZTRTXGIDTMP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HJMZMZRCABDKKV-UHFFFAOYSA-M cyanoformate Chemical compound [O-]C(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-M 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- XHXOLHROLSADIX-UHFFFAOYSA-N n,n'-dibenzyl-2-bromopropanediamide Chemical compound C=1C=CC=CC=1CNC(=O)C(Br)C(=O)NCC1=CC=CC=C1 XHXOLHROLSADIX-UHFFFAOYSA-N 0.000 description 2
- YYAQOJILQOVUSK-UHFFFAOYSA-N n,n'-diphenylpropanediamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)NC1=CC=CC=C1 YYAQOJILQOVUSK-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ODOJAEHIIFIICL-UHFFFAOYSA-N 2-bromo-N,N'-diethylpropanediamide Chemical compound C(C)NC(C(C(=O)NCC)Br)=O ODOJAEHIIFIICL-UHFFFAOYSA-N 0.000 description 1
- SAHJOSKPGKTZTC-UHFFFAOYSA-N 5h-pyrrolo[3,4-d]pyrimidine Chemical compound C1=NC=C2CN=CC2=N1 SAHJOSKPGKTZTC-UHFFFAOYSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IDRIISKVLZHPDP-UHFFFAOYSA-N butyl cyanoformate Chemical compound CCCCOC(=O)C#N IDRIISKVLZHPDP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OBWFJXLKRAFEDI-UHFFFAOYSA-N methyl cyanoformate Chemical compound COC(=O)C#N OBWFJXLKRAFEDI-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- KEWOIBUJAMSMSU-UHFFFAOYSA-N propyl cyanoformate Chemical compound CCCOC(=O)C#N KEWOIBUJAMSMSU-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15807681A JPS5859967A (ja) | 1981-10-06 | 1981-10-06 | アミノマレイミド類の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15807681A JPS5859967A (ja) | 1981-10-06 | 1981-10-06 | アミノマレイミド類の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5859967A JPS5859967A (ja) | 1983-04-09 |
| JPS645592B2 true JPS645592B2 (it) | 1989-01-31 |
Family
ID=15663765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15807681A Granted JPS5859967A (ja) | 1981-10-06 | 1981-10-06 | アミノマレイミド類の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5859967A (it) |
-
1981
- 1981-10-06 JP JP15807681A patent/JPS5859967A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5859967A (ja) | 1983-04-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3895028A (en) | Alpha-(2-phenylbenzothiazol-5-yl)propionic acid | |
| Chatterjee et al. | Iron (III)-catalyzed synthesis of selenoesters from α-amino carbonyl derivatives at room temperature | |
| WO1997000867A1 (en) | Process for producing guanidine derivatives, intermediates therefor and their production | |
| US5498711A (en) | Synthesis of 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,903,11]dodecane | |
| US3481948A (en) | 2,2 - disubstituted - 3 - acyl - 5alpha - azidothiazolidine-4-carboxylic acids and derivatives | |
| EP0006999B1 (en) | A process for the production of 2-chlorobenzonitrile derivatives | |
| EP0052333A1 (en) | 4-Fluoro-5-oxypyrazole derivate and preparation thereof | |
| AU737994B2 (en) | Process for preparing o-(3-amino-2-hydroxy-propyl)-hydroxymic acid halides | |
| JPS645592B2 (it) | ||
| US4200757A (en) | Process for the production of 3-aminoisoxazoles | |
| US4521616A (en) | Method for the preparation of fluoroanthranilic acids | |
| GB1571990A (en) | Process for the preparation of cyanoacetic acid anilide derivatives | |
| US5233045A (en) | Process for the preparation of imidazothiazolone derivatives | |
| CN107857729B (zh) | 一种4-碘化-n-芳基化的吡唑类化合物的合成方法 | |
| US4009178A (en) | Brominating and oxidizing agent and method of using same | |
| FI69838C (fi) | Foerfarande foer framstaellning av 1,2,3-tiadiazol-5-ylurinaemnen | |
| JPS5914461B2 (ja) | ５−メルカプト−１，２，３−トリアゾ−ルの製法 | |
| EP0220025A1 (en) | 3-perfluoroalkyl-5-hydroxyisoxazoles | |
| EP0119091A2 (en) | 2,2-Diethoxypropionic acid derivatives | |
| KR940010282B1 (ko) | 시아노 구아니딘 유도체와 그 제조법 | |
| JPH0216309B2 (it) | ||
| EP0141560B1 (en) | Chemical process | |
| US3262948A (en) | 21, 21-ethylene-progesterone and process for the production thereof | |
| SU1490113A1 (ru) | Способ получени бис-(2,2,2-тринитроэтил)-тионкарбоната | |
| JPH06228103A (ja) | 新規なオクタヒドロアクリジン誘導体とその製造方法 |