IL31666A - Process for the resolution of 6-phenyl-2,3,5,6-tetrahydroimidazo(2,1-b)thiazole - Google Patents
Process for the resolution of 6-phenyl-2,3,5,6-tetrahydroimidazo(2,1-b)thiazoleInfo
- Publication number
- IL31666A IL31666A IL31666A IL3166669A IL31666A IL 31666 A IL31666 A IL 31666A IL 31666 A IL31666 A IL 31666A IL 3166669 A IL3166669 A IL 3166669A IL 31666 A IL31666 A IL 31666A
- Authority
- IL
- Israel
- Prior art keywords
- phenyl
- fractional
- thiazole
- process according
- separation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- HLFSDGLLUJUHTE-UHFFFAOYSA-N 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SCCN2CC1C1=CC=CC=C1 HLFSDGLLUJUHTE-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 230000003287 optical effect Effects 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Chemical class 0.000 claims description 10
- 230000007935 neutral effect Effects 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- OCQAXYHNMWVLRH-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical class C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 OCQAXYHNMWVLRH-UHFFFAOYSA-N 0.000 claims description 2
- -1 alkali metal salt Chemical class 0.000 claims description 2
- 238000001640 fractional crystallisation Methods 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical class C* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 230000000507 anthelmentic effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- UMZCLZPXPCNKML-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole Chemical compound C1=NC2=NCSC2=N1 UMZCLZPXPCNKML-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N25/00—Investigating or analyzing materials by the use of thermal means
- G01N25/56—Investigating or analyzing materials by the use of thermal means by investigating moisture content
- G01N25/62—Investigating or analyzing materials by the use of thermal means by investigating moisture content by psychrometric means, e.g. wet-and-dry bulb thermometers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR140702 | 1968-02-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31666A0 IL31666A0 (en) | 1969-04-30 |
| IL31666A true IL31666A (en) | 1973-01-30 |
Family
ID=8646288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31666A IL31666A (en) | 1968-02-21 | 1969-02-20 | Process for the resolution of 6-phenyl-2,3,5,6-tetrahydroimidazo(2,1-b)thiazole |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT284117B (en)) |
| BE (1) | BE728719A (en)) |
| CH (1) | CH495928A (en)) |
| DE (1) | DE1908802A1 (en)) |
| DK (1) | DK132436C (en)) |
| ES (1) | ES363928A1 (en)) |
| FI (1) | FI49424C (en)) |
| FR (1) | FR1577314A (en)) |
| GB (1) | GB1226253A (en)) |
| IL (1) | IL31666A (en)) |
| NL (1) | NL6902275A (en)) |
| SE (1) | SE365520B (en)) |
| YU (1) | YU33287B (en)) |
-
1968
- 1968-02-21 FR FR140702A patent/FR1577314A/fr not_active Expired
-
1969
- 1969-01-28 FI FI690262A patent/FI49424C/fi active
- 1969-02-13 NL NL6902275A patent/NL6902275A/xx unknown
- 1969-02-20 SE SE02368/69A patent/SE365520B/xx unknown
- 1969-02-20 BE BE728719D patent/BE728719A/xx not_active IP Right Cessation
- 1969-02-20 CH CH262669A patent/CH495928A/fr not_active IP Right Cessation
- 1969-02-20 GB GB1226253D patent/GB1226253A/en not_active Expired
- 1969-02-20 DK DK96569*#A patent/DK132436C/da not_active IP Right Cessation
- 1969-02-20 IL IL31666A patent/IL31666A/en unknown
- 1969-02-21 DE DE19691908802 patent/DE1908802A1/de not_active Withdrawn
- 1969-02-21 AT AT177769A patent/AT284117B/de not_active IP Right Cessation
- 1969-02-21 ES ES363928A patent/ES363928A1/es not_active Expired
- 1969-02-21 YU YU411/69A patent/YU33287B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES363928A1 (es) | 1971-01-01 |
| FI49424B (en)) | 1975-02-28 |
| YU33287B (en) | 1976-08-31 |
| BE728719A (en)) | 1969-08-20 |
| SE365520B (en)) | 1974-03-25 |
| DE1908802A1 (de) | 1969-11-06 |
| AT284117B (de) | 1970-09-10 |
| DK132436C (da) | 1976-05-10 |
| YU41169A (en) | 1976-03-31 |
| FR1577314A (en)) | 1969-08-08 |
| IL31666A0 (en) | 1969-04-30 |
| FI49424C (fi) | 1975-06-10 |
| DK132436B (da) | 1975-12-08 |
| CH495928A (fr) | 1970-09-15 |
| GB1226253A (en)) | 1971-03-24 |
| NL6902275A (en)) | 1969-08-25 |
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