JPS63218682A - スルフエンアミドを用いる含窒素化合物の製造方法 - Google Patents
スルフエンアミドを用いる含窒素化合物の製造方法Info
- Publication number
- JPS63218682A JPS63218682A JP62053702A JP5370287A JPS63218682A JP S63218682 A JPS63218682 A JP S63218682A JP 62053702 A JP62053702 A JP 62053702A JP 5370287 A JP5370287 A JP 5370287A JP S63218682 A JPS63218682 A JP S63218682A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- sulfenamide
- ring
- heterocyclic
- 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.)
- Granted
Links
- -1 nitrogen-containing compound Chemical class 0.000 title claims abstract description 37
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 5
- 150000001768 cations Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- XQIJUNRYEIASNK-UHFFFAOYSA-N amino carbamodithioate Chemical class NSC(N)=S XQIJUNRYEIASNK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 238000006049 ring expansion reaction Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- XNEHEHDIBXHYCM-UHFFFAOYSA-N amino n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SN XNEHEHDIBXHYCM-UHFFFAOYSA-N 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- GBHHZAUQJNATAT-UHFFFAOYSA-N dimethylamino carbamodithioate Chemical compound CN(C)SC(N)=S GBHHZAUQJNATAT-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000003595 spectral effect Effects 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
- WIKVRBTVPSOQHJ-UHFFFAOYSA-N 2h-1,5,2-dithiazine Chemical compound C1SNC=CS1 WIKVRBTVPSOQHJ-UHFFFAOYSA-N 0.000 description 1
- UHYXLMSQKBEYKM-UHFFFAOYSA-M 4-(5-phenyl-1,3-oxathiol-2-ylidene)morpholin-4-ium perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1COCC[N+]1=C1SC=C(C=2C=CC=CC=2)O1 UHYXLMSQKBEYKM-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- JTQBVADRAHBUPK-UHFFFAOYSA-N C1COCCN1C1=NSC(C=2C=CC=CC=2)=NS1 Chemical compound C1COCCN1C1=NSC(C=2C=CC=CC=2)=NS1 JTQBVADRAHBUPK-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical class C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 1
- KYYBWOQFPMAZAU-UHFFFAOYSA-N amino morpholine-4-carbodithioate Chemical compound NSC(=S)N1CCOCC1 KYYBWOQFPMAZAU-UHFFFAOYSA-N 0.000 description 1
- JGBDWRSVCOWWAD-UHFFFAOYSA-N amino n,n-diethylcarbamodithioate Chemical compound CCN(CC)C(=S)SN JGBDWRSVCOWWAD-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- LEXXWUCMDYEREL-UHFFFAOYSA-N imino(diphenyl)-$l^{4}-sulfane Chemical class C=1C=CC=CC=1S(=N)C1=CC=CC=C1 LEXXWUCMDYEREL-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 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
- NEQRDYYMIIIVPW-UHFFFAOYSA-N s-amino benzenecarbothioate Chemical compound NSC(=O)C1=CC=CC=C1 NEQRDYYMIIIVPW-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- GLBQVJGBPFPMMV-UHFFFAOYSA-N sulfilimine Chemical compound S=N GLBQVJGBPFPMMV-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62053702A JPS63218682A (ja) | 1987-03-09 | 1987-03-09 | スルフエンアミドを用いる含窒素化合物の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62053702A JPS63218682A (ja) | 1987-03-09 | 1987-03-09 | スルフエンアミドを用いる含窒素化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63218682A true JPS63218682A (ja) | 1988-09-12 |
| JPH0560830B2 JPH0560830B2 (Direct) | 1993-09-03 |
Family
ID=12950156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62053702A Granted JPS63218682A (ja) | 1987-03-09 | 1987-03-09 | スルフエンアミドを用いる含窒素化合物の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63218682A (Direct) |
-
1987
- 1987-03-09 JP JP62053702A patent/JPS63218682A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0560830B2 (Direct) | 1993-09-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |