DE166448C - - Google Patents
Info
- Publication number
- DE166448C DE166448C DE1904166448D DE166448DA DE166448C DE 166448 C DE166448 C DE 166448C DE 1904166448 D DE1904166448 D DE 1904166448D DE 166448D A DE166448D A DE 166448DA DE 166448 C DE166448 C DE 166448C
- Authority
- DE
- Germany
- Prior art keywords
- alcohol
- urea
- water
- malonitrile
- diethyl
- 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 - Lifetime
Links
- 239000002253 acid Substances 0.000 claims description 5
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- TYXNQDAIWMHZAY-UHFFFAOYSA-N [C].NC(N)=O Chemical compound [C].NC(N)=O TYXNQDAIWMHZAY-UHFFFAOYSA-N 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000004202 carbamide Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 229960000583 Acetic Acid Drugs 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- DPHBCBNBDNTWKL-UHFFFAOYSA-N C(C)C(C(C#N)O)(C#N)CC Chemical compound C(C)C(C(C#N)O)(C#N)CC DPHBCBNBDNTWKL-UHFFFAOYSA-N 0.000 description 3
- 150000007656 barbituric acids Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AIEHSKCCVPIDNR-UHFFFAOYSA-N 2,2-diethylpropanedinitrile Chemical compound CCC(CC)(C#N)C#N AIEHSKCCVPIDNR-UHFFFAOYSA-N 0.000 description 2
- MKVPMUGXGFJVML-UHFFFAOYSA-N C(CC)C(C(C#N)O)(C#N)CCC Chemical compound C(CC)C(C(C#N)O)(C#N)CCC MKVPMUGXGFJVML-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GKRZNOGGALENQJ-UHFFFAOYSA-N N-carbamoylacetamide Chemical compound CC(=O)NC(N)=O GKRZNOGGALENQJ-UHFFFAOYSA-N 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N Sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- -1 chlorine platinum Chemical compound 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001376 precipitating Effects 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- ZYYONKUXELBUET-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-10-fluoro-1,3,4,5,6,7-hexahydrobenzo[1,2]cyclohepta[6,7-d]pyrimidine-2-thione Chemical compound C1=C(OC)C(OC)=CC=C1C1C(CCCC=2C3=CC(F)=CC=2)=C3NC(=S)N1 ZYYONKUXELBUET-UHFFFAOYSA-N 0.000 description 1
- FTOAOBMCPZCFFF-UHFFFAOYSA-N Barbital Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 1
- 229960002319 Barbital Drugs 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- RCOUWKSZRXJXLA-UHFFFAOYSA-N Propylbarbital Chemical compound CCCC1(CCC)C(=O)NC(=O)NC1=O RCOUWKSZRXJXLA-UHFFFAOYSA-N 0.000 description 1
- 229940083082 Pyrimidine derivatives acting on arteriolar smooth muscle Drugs 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- C07D239/48—Two nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT25221D AT25221B (de) | 1904-02-10 | 1905-09-06 | Verfahren zur Darstellung von Diiminobarbitursäuren. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE166448C true DE166448C (no) |
Family
ID=431841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1904166448D Expired - Lifetime DE166448C (no) | 1904-02-10 | 1904-02-10 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE166448C (no) |
-
1904
- 1904-02-10 DE DE1904166448D patent/DE166448C/de not_active Expired - Lifetime
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