DE1770751A1 - Verfahren zur Herstellung von 1-Benzylcycloheptimidazol-2(1H)-on und seinen Derivaten - Google Patents
Verfahren zur Herstellung von 1-Benzylcycloheptimidazol-2(1H)-on und seinen DerivatenInfo
- Publication number
- DE1770751A1 DE1770751A1 DE19681770751 DE1770751A DE1770751A1 DE 1770751 A1 DE1770751 A1 DE 1770751A1 DE 19681770751 DE19681770751 DE 19681770751 DE 1770751 A DE1770751 A DE 1770751A DE 1770751 A1 DE1770751 A1 DE 1770751A1
- Authority
- DE
- Germany
- Prior art keywords
- basic substance
- reaction
- sodium
- temperature
- minutes
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 4
- PUDJZXFLQHLFGS-UHFFFAOYSA-N 1-benzylcyclohepta[d]imidazol-2-one Chemical compound O=C1N=C2C=CC=CC=C2N1CC1=CC=CC=C1 PUDJZXFLQHLFGS-UHFFFAOYSA-N 0.000 title description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- -1 aliphatic alcohols Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical class O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HBNPHVRKFGNYAV-UHFFFAOYSA-N 1h-cyclohepta[d]imidazol-2-one Chemical class C1=CC=CC=C2NC(=O)N=C21 HBNPHVRKFGNYAV-UHFFFAOYSA-N 0.000 description 1
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000920033 Eugenes Species 0.000 description 1
- 241001233242 Lontra Species 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3080767A GB1191686A (en) | 1967-07-04 | 1967-07-04 | Process for the Preparation of Cycloheptimidazolone Derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1770751A1 true DE1770751A1 (de) | 1971-12-09 |
Family
ID=10313444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681770751 Pending DE1770751A1 (de) | 1967-07-04 | 1968-06-29 | Verfahren zur Herstellung von 1-Benzylcycloheptimidazol-2(1H)-on und seinen Derivaten |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE717342A (cs) |
| BR (1) | BR6800375D0 (cs) |
| CH (1) | CH482683A (cs) |
| DE (1) | DE1770751A1 (cs) |
| ES (1) | ES355662A1 (cs) |
| FR (1) | FR1575980A (cs) |
| GB (1) | GB1191686A (cs) |
| NL (1) | NL6809402A (cs) |
-
1967
- 1967-07-04 GB GB3080767A patent/GB1191686A/en not_active Expired
-
1968
- 1968-06-28 BE BE717342D patent/BE717342A/xx unknown
- 1968-06-29 DE DE19681770751 patent/DE1770751A1/de active Pending
- 1968-07-01 ES ES355662A patent/ES355662A1/es not_active Expired
- 1968-07-03 NL NL6809402A patent/NL6809402A/xx unknown
- 1968-07-03 BR BR20037568A patent/BR6800375D0/pt unknown
- 1968-07-03 CH CH990168A patent/CH482683A/fr not_active IP Right Cessation
- 1968-07-04 FR FR1575980D patent/FR1575980A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6809402A (cs) | 1969-01-07 |
| GB1191686A (en) | 1970-05-13 |
| CH482683A (fr) | 1969-12-15 |
| BR6800375D0 (pt) | 1973-02-13 |
| FR1575980A (cs) | 1969-07-25 |
| BE717342A (cs) | 1968-12-02 |
| ES355662A1 (es) | 1969-12-16 |
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