JPS60115554A - デアセチルモキシシリトの製造方法 - Google Patents
デアセチルモキシシリトの製造方法Info
- Publication number
- JPS60115554A JPS60115554A JP22309983A JP22309983A JPS60115554A JP S60115554 A JPS60115554 A JP S60115554A JP 22309983 A JP22309983 A JP 22309983A JP 22309983 A JP22309983 A JP 22309983A JP S60115554 A JPS60115554 A JP S60115554A
- Authority
- JP
- Japan
- Prior art keywords
- dam
- dimethylethylamine
- methylphenoxy
- isopropyl
- purity
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- HJGRPZCEBPNMDU-UHFFFAOYSA-N 4-[2-(dimethylamino)ethoxy]-2-methyl-5-propan-2-ylphenol Chemical compound CC(C)C1=CC(O)=C(C)C=C1OCCN(C)C HJGRPZCEBPNMDU-UHFFFAOYSA-N 0.000 title description 2
- 238000006193 diazotization reaction Methods 0.000 claims abstract description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract 2
- -1 5-methylphenoxy Chemical group 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 238000005292 vacuum distillation Methods 0.000 claims description 7
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 7
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 3
- 235000010288 sodium nitrite Nutrition 0.000 abstract description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract description 2
- 239000000219 Sympatholytic Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000002526 effect on cardiovascular system Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical class CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 abstract 1
- 210000000056 organ Anatomy 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 238000001816 cooling Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000199 molecular distillation Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000005844 Thymol Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229960000790 thymol Drugs 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- SCBMXGBZXCDNLH-UHFFFAOYSA-N 2-amino-3-methyl-6-propan-2-ylphenol Chemical compound CC(C)C1=CC=C(C)C(N)=C1O SCBMXGBZXCDNLH-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- IPWGSXZCDPTDEH-UHFFFAOYSA-N Moxisylyte hydrochloride Chemical compound [Cl-].CC(C)C1=CC(OC(C)=O)=C(C)C=C1OCC[NH+](C)C IPWGSXZCDPTDEH-UHFFFAOYSA-N 0.000 description 1
- 101100346764 Mus musculus Mtln gene Proteins 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22309983A JPS60115554A (ja) | 1983-11-29 | 1983-11-29 | デアセチルモキシシリトの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22309983A JPS60115554A (ja) | 1983-11-29 | 1983-11-29 | デアセチルモキシシリトの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60115554A true JPS60115554A (ja) | 1985-06-22 |
| JPS6224416B2 JPS6224416B2 (US20030199744A1-20031023-C00003.png) | 1987-05-28 |
Family
ID=16792807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22309983A Granted JPS60115554A (ja) | 1983-11-29 | 1983-11-29 | デアセチルモキシシリトの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60115554A (US20030199744A1-20031023-C00003.png) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0694300A1 (en) * | 1994-07-27 | 1996-01-31 | Institut De Recherches Chimiques Et Biologiques Appliquees (Irceba) | Treatment of impotence |
| EP0728479A1 (en) * | 1995-02-21 | 1996-08-28 | Institut De Recherches Chimiques Et Biologiques Appliquees (Irceba) | Deacetyl moxisylyte in the treatment of acute urinary retention |
| CN109134281A (zh) * | 2018-08-27 | 2019-01-04 | 浙江山峪科技股份有限公司 | 间二烷胺基苯酚的合成方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0356964Y2 (US20030199744A1-20031023-C00003.png) * | 1987-01-19 | 1991-12-25 |
-
1983
- 1983-11-29 JP JP22309983A patent/JPS60115554A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0694300A1 (en) * | 1994-07-27 | 1996-01-31 | Institut De Recherches Chimiques Et Biologiques Appliquees (Irceba) | Treatment of impotence |
| EP0728479A1 (en) * | 1995-02-21 | 1996-08-28 | Institut De Recherches Chimiques Et Biologiques Appliquees (Irceba) | Deacetyl moxisylyte in the treatment of acute urinary retention |
| CN109134281A (zh) * | 2018-08-27 | 2019-01-04 | 浙江山峪科技股份有限公司 | 间二烷胺基苯酚的合成方法 |
| CN109134281B (zh) * | 2018-08-27 | 2021-10-08 | 浙江山峪科技股份有限公司 | 间二烷胺基苯酚的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6224416B2 (US20030199744A1-20031023-C00003.png) | 1987-05-28 |
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