DE290522C - - Google Patents
Info
- Publication number
- DE290522C DE290522C DENDAT290522D DE290522DA DE290522C DE 290522 C DE290522 C DE 290522C DE NDAT290522 D DENDAT290522 D DE NDAT290522D DE 290522D A DE290522D A DE 290522DA DE 290522 C DE290522 C DE 290522C
- Authority
- DE
- Germany
- Prior art keywords
- urethane
- parts
- alcohol
- dilute
- heated
- 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.)
- Active
Links
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000003673 urethanes Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- AYQVGLKNEIAJIN-UHFFFAOYSA-N ethyl N-benzoyl-N-nitrocarbamate Chemical compound [N+](=O)([O-])N(C(=O)OCC)C(C1=CC=CC=C1)=O AYQVGLKNEIAJIN-UHFFFAOYSA-N 0.000 description 3
- QKDNLXJEQGRZEV-UHFFFAOYSA-N ethyl n-benzoylcarbamate Chemical compound CCOC(=O)NC(=O)C1=CC=CC=C1 QKDNLXJEQGRZEV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 2
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- -1 p-Monoaminobenzoylurethane Chemical compound 0.000 description 2
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- IDIFJUBLWASPDU-UHFFFAOYSA-N 2-(diethylamino)ethyl acetate Chemical group CCN(CC)CCOC(C)=O IDIFJUBLWASPDU-UHFFFAOYSA-N 0.000 description 1
- KJSGODDTWRXQRH-UHFFFAOYSA-N 2-(dimethylamino)ethyl benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC=C1 KJSGODDTWRXQRH-UHFFFAOYSA-N 0.000 description 1
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 229940052296 esters of benzoic acid for local anesthesia Drugs 0.000 description 1
- DIPBOVZOVZAKGI-UHFFFAOYSA-N ethyl carbamate;sodium Chemical compound [Na].CCOC(N)=O DIPBOVZOVZAKGI-UHFFFAOYSA-N 0.000 description 1
- KSCNGTHSLMJGRH-UHFFFAOYSA-N ethyl n-(4-nitrobenzoyl)carbamate Chemical group CCOC(=O)NC(=O)C1=CC=C([N+]([O-])=O)C=C1 KSCNGTHSLMJGRH-UHFFFAOYSA-N 0.000 description 1
- CLLOFODTUXGHHT-UHFFFAOYSA-N ethyl n-acetylcarbamate Chemical compound CCOC(=O)NC(C)=O CLLOFODTUXGHHT-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE290522C true DE290522C (enrdf_load_stackoverflow) |
Family
ID=545482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT290522D Active DE290522C (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE290522C (enrdf_load_stackoverflow) |
-
0
- DE DENDAT290522D patent/DE290522C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE290522C (enrdf_load_stackoverflow) | ||
| AT72462B (de) | Verfahren zur Darstellung von Estern der Alkamine. | |
| DE2412323A1 (de) | 1,2-diphenyl-aethanderivate, verfahren zu ihrer herstellung und ihre verwendung | |
| DE223796C (enrdf_load_stackoverflow) | ||
| AT299169B (de) | Verfahren zur Herstellung der neuen α-[p-(1-Cyclohexenyl)-phenyl]-propionsäure | |
| DE1039063B (de) | Verfahren zur Herstellung eines antipyretisch wirksamen, substituierten 1, 2-Diphenyl-3, 5-dioxo-pyrazolidins und dessen Salzen | |
| DE575470C (de) | Verfahren zur Darstellung von C, C-disubstituierten Derivaten der Barbitursaeure | |
| DE266788C (enrdf_load_stackoverflow) | ||
| DE510452C (de) | Verfahren zur Darstellung von 2, 4'-Oxyarylaminonaphthalincarbonsaeuren | |
| AT228211B (de) | Verfahren zur Herstellung von neuen Phenothiazinderivaten, sowie von Säureadditionssalzen und quartären Salzen dieser Phenothiazinderivate | |
| DE525654C (de) | Verfahren zur Darstellung einer o-Amino-p-Kresolcarbondaeure | |
| AT254209B (de) | Verfahren zur Herstellung von neuen 1-(Cyclopropylcarbonyl)-harnstoffen | |
| DE1200832B (de) | Verfahren zur Herstellung von 3, 5-Dijodthyroninderivaten | |
| DE1221646B (de) | Verfahren zur Herstellung von 3, 5-Dijodthyroninen | |
| CH326786A (de) | Verfahren zur Herstellung eines neuen Esters | |
| DE1234711B (de) | Verfahren zur Herstellung von 1-(Cyclopropylcarbonyl)-harnstoffen | |
| DE212901C (enrdf_load_stackoverflow) | ||
| AT227256B (de) | Verfahren zur Herstellung von neuen Aminoindanen und deren Salzen | |
| DE820307C (de) | Verfahren zur Herstellung von neuen Naphthylpropionsaeuren und ihren funktionellen Derivaten | |
| DE963776C (de) | Verfahren zur Herstellung von antiphlogistisch wirksamen ª‡-Amino-ª‰-oxycarbonsaeureaniliden | |
| DE230043C (enrdf_load_stackoverflow) | ||
| AT32639B (de) | Verfahren zur Darstellung von Methylenzitrylsalizylsäure. | |
| DE892447C (de) | Verfahren zur Herstellung von Dicyclohexylaethanverbindungen | |
| AT238171B (de) | Verfahren zur Herstellung von N-(2,3-Dimethylphenyl)-anthranilsäure und deren Salzen | |
| AT207383B (de) | Verfahren zur Herstellung von Sulfonylharnstoffen |