CH411901A - Verfahren zur Herstellung von heterocyclischen Verbindungen - Google Patents
Verfahren zur Herstellung von heterocyclischen VerbindungenInfo
- Publication number
- CH411901A CH411901A CH1135661A CH1135661A CH411901A CH 411901 A CH411901 A CH 411901A CH 1135661 A CH1135661 A CH 1135661A CH 1135661 A CH1135661 A CH 1135661A CH 411901 A CH411901 A CH 411901A
- Authority
- CH
- Switzerland
- Prior art keywords
- allyl
- myristyl
- acid
- malonic ester
- thiourea
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 3
- -1 alkyl radical Chemical class 0.000 claims description 13
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 159000000007 calcium salts Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZLAJEWCTXKXIPN-UHFFFAOYSA-N 3-dodecoxy-3-oxopropanoic acid Chemical compound CCCCCCCCCCCCOC(=O)CC(O)=O ZLAJEWCTXKXIPN-UHFFFAOYSA-N 0.000 description 1
- BXVYHGJHTBTHCR-UHFFFAOYSA-N 3-oxo-3-tetradecoxypropanoic acid Chemical compound CCCCCCCCCCCCCCOC(=O)CC(O)=O BXVYHGJHTBTHCR-UHFFFAOYSA-N 0.000 description 1
- BYTREEXLNFPWOK-UHFFFAOYSA-N 3-oxo-3-undecoxypropanoic acid Chemical compound CCCCCCCCCCCOC(=O)CC(O)=O BYTREEXLNFPWOK-UHFFFAOYSA-N 0.000 description 1
- OVHMYBVWONTHHS-UHFFFAOYSA-N 5-butyl-2-sulfanylidene-5-tetradecyl-1,3-diazinane-4,6-dione Chemical compound C(CCC)C1(C(NC(NC1=O)=S)=O)CCCCCCCCCCCCCC OVHMYBVWONTHHS-UHFFFAOYSA-N 0.000 description 1
- IIHQNRFNNXWUDM-UHFFFAOYSA-N 5-methyl-2-sulfanylidene-5-tetradecyl-1,3-diazinane-4,6-dione Chemical compound CC1(C(NC(NC1=O)=S)=O)CCCCCCCCCCCCCC IIHQNRFNNXWUDM-UHFFFAOYSA-N 0.000 description 1
- OENFDZLHKRDAFJ-UHFFFAOYSA-N 5-propyl-2-sulfanylidene-5-tetradecyl-1,3-diazinane-4,6-dione Chemical compound C(CC)C1(C(NC(NC1=O)=S)=O)CCCCCCCCCCCCCC OENFDZLHKRDAFJ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- AWKWKLZVORHVNA-UHFFFAOYSA-N diethyl 2-(2-methylpropyl)-2-tetradecylpropanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCCCCCCCCCC)CC(C)C)=O AWKWKLZVORHVNA-UHFFFAOYSA-N 0.000 description 1
- JMFSXDXYJBOUOC-UHFFFAOYSA-N diethyl 2-butyl-2-tetradecylpropanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCCCCCCCCCC)CCCC)=O JMFSXDXYJBOUOC-UHFFFAOYSA-N 0.000 description 1
- HWYDOMRWYZLZMS-UHFFFAOYSA-N diethyl 2-cyclohexyl-2-tetradecylpropanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCCCCCCCCCC)C1CCCCC1)=O HWYDOMRWYZLZMS-UHFFFAOYSA-N 0.000 description 1
- GMFYSFDTMNXERW-UHFFFAOYSA-N diethyl 2-methyl-2-tetradecylpropanedioate Chemical compound CCCCCCCCCCCCCCC(C)(C(=O)OCC)C(=O)OCC GMFYSFDTMNXERW-UHFFFAOYSA-N 0.000 description 1
- GDWAYKGILJJNBB-UHFFFAOYSA-N diethyl 2-prop-2-enylpropanedioate Chemical compound CCOC(=O)C(CC=C)C(=O)OCC GDWAYKGILJJNBB-UHFFFAOYSA-N 0.000 description 1
- FAUMICYNAVPLTD-UHFFFAOYSA-N diethyl 2-prop-2-ynyl-2-tetradecylpropanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCCCCCCCCCC)CC#C)=O FAUMICYNAVPLTD-UHFFFAOYSA-N 0.000 description 1
- OCSXBKKWNWCTDX-UHFFFAOYSA-N diethyl 2-propyl-2-tetradecylpropanedioate Chemical compound CCCCCCCCCCCCCCC(CCC)(C(=O)OCC)C(=O)OCC OCSXBKKWNWCTDX-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/66—Thiobarbituric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Medicinal Preparation (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1135661A CH411901A (de) | 1961-09-29 | 1961-09-29 | Verfahren zur Herstellung von heterocyclischen Verbindungen |
| CH345366A CH427819A (de) | 1961-09-29 | 1962-07-19 | Verfahren zur Herstellung von heterocyclischen Verbindungen |
| BE622081A BE622081A (fr) | 1961-09-29 | 1962-09-04 | Procédé pour la préparation de composés hétérocycliques |
| GB3652662A GB973922A (en) | 1961-09-29 | 1962-09-26 | Novel thiobarbituric acid derivatives and a process for the manufacture thereof |
| ES281138A ES281138A1 (es) | 1961-09-29 | 1962-09-28 | Procedimiento para la preparación de compuestos heterocíclicos |
| MY6500153A MY6500153A (en) | 1961-09-29 | 1965-12-31 | Novel thiobarbituric acid derivatives and a process for the manufacture thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1135661A CH411901A (de) | 1961-09-29 | 1961-09-29 | Verfahren zur Herstellung von heterocyclischen Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH411901A true CH411901A (de) | 1966-04-30 |
Family
ID=4372699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1135661A CH411901A (de) | 1961-09-29 | 1961-09-29 | Verfahren zur Herstellung von heterocyclischen Verbindungen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE622081A (fr) |
| CH (1) | CH411901A (fr) |
| ES (1) | ES281138A1 (fr) |
| GB (1) | GB973922A (fr) |
| MY (1) | MY6500153A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0411277A3 (en) * | 1989-08-03 | 1991-08-28 | Huels Aktiengesellschaft | Process for preparation of na-thiobarbiturate |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5869494A (en) * | 1995-02-13 | 1999-02-09 | Gulliya; Kirpal S. | Uses for barbituric acid analogs |
| WO1996025402A1 (fr) * | 1995-02-13 | 1996-08-22 | Gulliya Kirpal S | Nouvelles utilisations d'analogues de l'acide barbiturique |
-
1961
- 1961-09-29 CH CH1135661A patent/CH411901A/de unknown
-
1962
- 1962-09-04 BE BE622081A patent/BE622081A/fr unknown
- 1962-09-26 GB GB3652662A patent/GB973922A/en not_active Expired
- 1962-09-28 ES ES281138A patent/ES281138A1/es not_active Expired
-
1965
- 1965-12-31 MY MY6500153A patent/MY6500153A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0411277A3 (en) * | 1989-08-03 | 1991-08-28 | Huels Aktiengesellschaft | Process for preparation of na-thiobarbiturate |
Also Published As
| Publication number | Publication date |
|---|---|
| MY6500153A (en) | 1965-12-31 |
| GB973922A (en) | 1964-11-04 |
| ES281138A1 (es) | 1963-04-01 |
| BE622081A (fr) | 1963-03-04 |
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