DE2065955C3 - Verfahren zur Herstellung von 1-(2-Thiazolyl)-2-oxotetrahydroimidazol - Google Patents
Verfahren zur Herstellung von 1-(2-Thiazolyl)-2-oxotetrahydroimidazolInfo
- Publication number
- DE2065955C3 DE2065955C3 DE19702065955 DE2065955A DE2065955C3 DE 2065955 C3 DE2065955 C3 DE 2065955C3 DE 19702065955 DE19702065955 DE 19702065955 DE 2065955 A DE2065955 A DE 2065955A DE 2065955 C3 DE2065955 C3 DE 2065955C3
- Authority
- DE
- Germany
- Prior art keywords
- thiazolyl
- oxotetrahydroimidazole
- reaction
- urethane
- urethanes
- 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
- 238000000034 method Methods 0.000 title claims description 42
- 230000008569 process Effects 0.000 title claims description 30
- OQEJNPNAYASGQD-UHFFFAOYSA-N 1-(1,3-thiazol-2-yl)imidazolidin-2-one Chemical compound O=C1NCCN1C1=NC=CS1 OQEJNPNAYASGQD-UHFFFAOYSA-N 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000006243 chemical reaction Methods 0.000 description 12
- UGOCIZBVCIURJA-UHFFFAOYSA-N ethyl n-(1,3-thiazol-2-yl)carbamate Chemical compound CCOC(=O)NC1=NC=CS1 UGOCIZBVCIURJA-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- 150000003673 urethanes Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000012552 review Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- KQMBDBQMFJVWAX-UHFFFAOYSA-N 1-(2-chloroethyl)-3-(1,3-thiazol-2-yl)urea Chemical compound ClCCNC(=O)NC1=NC=CS1 KQMBDBQMFJVWAX-UHFFFAOYSA-N 0.000 description 4
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BGFLDMAWPFQQGF-UHFFFAOYSA-N S1C(=NC=C1)N(C(=O)OCC)CCN Chemical compound S1C(=NC=C1)N(C(=O)OCC)CCN BGFLDMAWPFQQGF-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- ADYWUAMYLMRHRL-UHFFFAOYSA-N ethyl n-(2-aminoethyl)carbamate Chemical compound CCOC(=O)NCCN ADYWUAMYLMRHRL-UHFFFAOYSA-N 0.000 description 2
- QHSHDVYEJKLXLB-UHFFFAOYSA-N ethyl n-(2-chloroethyl)carbamate Chemical compound CCOC(=O)NCCCl QHSHDVYEJKLXLB-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- WDJXDOCQCALXMV-UHFFFAOYSA-N hydron;1,3-thiazol-2-amine;chloride Chemical compound Cl.NC1=NC=CS1 WDJXDOCQCALXMV-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007725 thermal activation Methods 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GOGYHVOOMHFPAC-UHFFFAOYSA-N 1-butyl-1-phenylurea Chemical compound CCCCN(C(N)=O)C1=CC=CC=C1 GOGYHVOOMHFPAC-UHFFFAOYSA-N 0.000 description 1
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- MVMCMYDOBJLYLA-UHFFFAOYSA-N ethyl N-[2-(1,3-thiazol-2-yl)ethyl]carbamate Chemical compound CCOC(=O)NCCC1=NC=CS1 MVMCMYDOBJLYLA-UHFFFAOYSA-N 0.000 description 1
- SRBONAHFJNBPPA-UHFFFAOYSA-N ethyl N-ethyl-N-(1,3-thiazol-2-yl)carbamate Chemical compound S1C(=NC=C1)N(C(=O)OCC)CC SRBONAHFJNBPPA-UHFFFAOYSA-N 0.000 description 1
- HLUWOHKDIGVECG-UHFFFAOYSA-N ethyl N-phenyl-N-(1,3-thiazol-2-yl)carbamate Chemical compound S1C(=NC=C1)N(C(=O)OCC)C1=CC=CC=C1 HLUWOHKDIGVECG-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003349 semicarbazides Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- CKQORTPXQDLZGH-UHFFFAOYSA-N tetrazine-5,6-diamine Chemical compound NC1=NN=NN=C1N CKQORTPXQDLZGH-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO001099 | 1969-07-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2065955A1 DE2065955A1 (de) | 1977-05-18 |
| DE2065955B2 DE2065955B2 (de) | 1979-09-13 |
| DE2065955C3 true DE2065955C3 (de) | 1980-05-29 |
Family
ID=10996673
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702065955 Expired DE2065955C3 (de) | 1969-07-07 | 1970-07-07 | Verfahren zur Herstellung von 1-(2-Thiazolyl)-2-oxotetrahydroimidazol |
| DE19702033611 Expired DE2033611C3 (de) | 1969-07-07 | 1970-07-07 | Verfahren zur Herstellung von 1-(2-Thiazolyl)-2-oxotetrahydroimidazol |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702033611 Expired DE2033611C3 (de) | 1969-07-07 | 1970-07-07 | Verfahren zur Herstellung von 1-(2-Thiazolyl)-2-oxotetrahydroimidazol |
Country Status (5)
| Country | Link |
|---|---|
| AT (2) | AT300794B (enExample) |
| CH (2) | CH576977A5 (enExample) |
| DE (2) | DE2065955C3 (enExample) |
| DK (1) | DK131344B (enExample) |
| NL (1) | NL7010011A (enExample) |
-
1970
- 1970-07-06 DK DK351170A patent/DK131344B/da not_active IP Right Cessation
- 1970-07-07 DE DE19702065955 patent/DE2065955C3/de not_active Expired
- 1970-07-07 AT AT612370A patent/AT300794B/de not_active IP Right Cessation
- 1970-07-07 DE DE19702033611 patent/DE2033611C3/de not_active Expired
- 1970-07-07 CH CH160973A patent/CH576977A5/xx not_active IP Right Cessation
- 1970-07-07 AT AT765871A patent/AT303725B/de not_active IP Right Cessation
- 1970-07-07 CH CH1029670A patent/CH557838A/xx not_active IP Right Cessation
- 1970-07-07 NL NL7010011A patent/NL7010011A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2065955B2 (de) | 1979-09-13 |
| DK131344C (enExample) | 1975-11-24 |
| CH576977A5 (enExample) | 1976-06-30 |
| DK131344B (da) | 1975-06-30 |
| AT303725B (de) | 1972-12-11 |
| NL7010011A (enExample) | 1971-01-11 |
| DE2033611B2 (de) | 1979-07-19 |
| CH557838A (de) | 1975-01-15 |
| DE2033611C3 (de) | 1980-03-20 |
| DE2033611A1 (de) | 1971-01-14 |
| AT300794B (de) | 1972-08-10 |
| DE2065955A1 (de) | 1977-05-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |