SU474149A3 - Способ получени производных 2,3,5,6-тетрагидроимидазо(2,1-в) тиазола - Google Patents
Способ получени производных 2,3,5,6-тетрагидроимидазо(2,1-в) тиазолаInfo
- Publication number
- SU474149A3 SU474149A3 SU1469620A SU1469620A SU474149A3 SU 474149 A3 SU474149 A3 SU 474149A3 SU 1469620 A SU1469620 A SU 1469620A SU 1469620 A SU1469620 A SU 1469620A SU 474149 A3 SU474149 A3 SU 474149A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mixture
- tetrahydroimidazo
- solution
- preparing
- added
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 7
- NGKOCETVOBCCII-UHFFFAOYSA-N 2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole Chemical class C1CN=C2SCCN21 NGKOCETVOBCCII-UHFFFAOYSA-N 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Chemical class 0.000 description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- -1 2- (2-bromoethyl) -iminothiazolidine iodohydrate Chemical compound 0.000 description 3
- 125000005999 2-bromoethyl group Chemical group 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 239000002253 acid Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- BYMMIQCVDHHYGG-UHFFFAOYSA-N Cl.OP(O)(O)=O Chemical compound Cl.OP(O)(O)=O BYMMIQCVDHHYGG-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- WCHLYCOBWZVGLI-UHFFFAOYSA-N 2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole hydrobromide Chemical compound Br.S1C=2N(CC1)CCN2 WCHLYCOBWZVGLI-UHFFFAOYSA-N 0.000 description 1
- UMZCLZPXPCNKML-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole Chemical class C1=NC2=NCSC2=N1 UMZCLZPXPCNKML-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical class C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940058300 antinematodal imidazothiazole derivative Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/18—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI000923 HU162754B (enrdf_load_stackoverflow) | 1969-10-01 | 1969-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU474149A3 true SU474149A3 (ru) | 1975-06-14 |
Family
ID=10994369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1469620A SU474149A3 (ru) | 1969-10-01 | 1970-07-30 | Способ получени производных 2,3,5,6-тетрагидроимидазо(2,1-в) тиазола |
Country Status (14)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2450010C2 (ru) * | 2006-03-10 | 2012-05-10 | Грюненталь Гмбх | ЗАМЕЩЕННЫЕ ИМИДАЗО[2,1-b]ТИАЗОЛЫ И ИХ ПРИМЕНЕНИЕ ДЛЯ ПРИГОТОВЛЕНИЯ ЛЕКАРСТВЕННЫХ СРЕДСТВ |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3359907A (en) * | 1965-06-24 | 1967-12-26 | Gen Electric | Centra-turbine pump |
-
0
- BE BE755204D patent/BE755204A/xx not_active IP Right Cessation
-
1969
- 1969-10-01 HU HUCI000923 patent/HU162754B/hu unknown
-
1970
- 1970-07-07 AT AT612470A patent/AT296978B/de active
- 1970-07-09 DE DE19702065854 patent/DE2065854C3/de not_active Expired
- 1970-07-17 GB GB3483770A patent/GB1313219A/en not_active Expired
- 1970-07-27 SE SE1031070A patent/SE375994B/xx unknown
- 1970-07-28 DK DK391970A patent/DK132706C/da not_active IP Right Cessation
- 1970-07-29 FR FR7028004A patent/FR2065842A5/fr not_active Expired
- 1970-07-30 SU SU1469620A patent/SU474149A3/ru active
- 1970-07-30 YU YU192070A patent/YU34242B/xx unknown
- 1970-09-01 NL NL7012909A patent/NL153546B/xx not_active IP Right Cessation
- 1970-09-17 CH CH1382970A patent/CH542234A/de not_active IP Right Cessation
- 1970-09-29 CS CS659570A patent/CS171334B1/cs unknown
- 1970-10-01 CA CA094542A patent/CA921924A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2450010C2 (ru) * | 2006-03-10 | 2012-05-10 | Грюненталь Гмбх | ЗАМЕЩЕННЫЕ ИМИДАЗО[2,1-b]ТИАЗОЛЫ И ИХ ПРИМЕНЕНИЕ ДЛЯ ПРИГОТОВЛЕНИЯ ЛЕКАРСТВЕННЫХ СРЕДСТВ |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2065854C3 (de) | 1978-08-24 |
| HU162754B (enrdf_load_stackoverflow) | 1973-04-28 |
| FR2065842A5 (enrdf_load_stackoverflow) | 1971-08-06 |
| BE755204A (enrdf_load_stackoverflow) | 1971-02-01 |
| GB1313219A (en) | 1973-04-11 |
| DK132706B (da) | 1976-01-26 |
| NL153546B (nl) | 1977-06-15 |
| DE2065854A1 (de) | 1976-07-08 |
| DE2065854B2 (de) | 1977-12-01 |
| CH542234A (de) | 1973-09-30 |
| CA921924A (en) | 1973-02-27 |
| AT296978B (de) | 1972-03-10 |
| SE375994B (enrdf_load_stackoverflow) | 1975-05-05 |
| DE2034081A1 (de) | 1971-04-08 |
| DE2034081B2 (de) | 1977-05-18 |
| DK132706C (da) | 1976-08-02 |
| CS171334B1 (enrdf_load_stackoverflow) | 1976-10-29 |
| NL7012909A (enrdf_load_stackoverflow) | 1971-04-05 |
| YU192070A (en) | 1978-10-31 |
| YU34242B (en) | 1979-04-30 |
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