DE917972C - Process for the manufacture of cyclic urethanes - Google Patents
Process for the manufacture of cyclic urethanesInfo
- Publication number
- DE917972C DE917972C DEB13985A DEB0013985A DE917972C DE 917972 C DE917972 C DE 917972C DE B13985 A DEB13985 A DE B13985A DE B0013985 A DEB0013985 A DE B0013985A DE 917972 C DE917972 C DE 917972C
- Authority
- DE
- Germany
- Prior art keywords
- cyclic urethanes
- amino alcohols
- phosgene
- cyclic
- manufacture
- 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
- -1 cyclic urethanes Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 5
- 150000001414 amino alcohols Chemical class 0.000 claims description 12
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 150000003840 hydrochlorides Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MFEVGQHCNVXMER-UHFFFAOYSA-L 1,3,2$l^{2}-dioxaplumbetan-4-one Chemical compound [Pb+2].[O-]C([O-])=O MFEVGQHCNVXMER-UHFFFAOYSA-L 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 description 1
- 229910000003 Lead carbonate Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 229940073579 ethanolamine hydrochloride Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- HWSZZLVAJGOAAY-UHFFFAOYSA-L lead(II) chloride Chemical compound Cl[Pb]Cl HWSZZLVAJGOAAY-UHFFFAOYSA-L 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Herstellung von cyclischen Urethanen Das Patent 883 go2 betrifft ein Verfahren zur Herstellung von cyclischen Urethanen durch Umsetzung von Aminoalkoholen mit mindestens einem Wasserstoffatom an der Aminogruppe mit Phosgen in wäBriger Lösung bei Anwesenheit von säurebindenden Mitteln.Process for Making Cyclic Urethanes The 883 patent go2 relates to a process for the production of cyclic urethanes by reaction of amino alcohols with at least one hydrogen atom on the amino group with phosgene in aqueous solution in the presence of acid-binding agents.
Es wurde nun gefunden, daB man in guter Ausbeute cyclische Urethane erhält, wenn man i Mol Phosgen auf etwa 3 Mol eines Aminoalkohols in organischen Lösungsmitteln, in welchen die Aminoalkohole und die sich bildenden cyclischen Urethane gut, dagegen die Hydrochloride der Aminoalkohole schwer löslich sind, ohne Zusatz sonstiger säurebindender Stoffe einwirken läBt; als Lösungsmittel haben sich neben anderen chlorierte Kohlenwasserstoffe, z. B. Chloroform und i, 4-Dichlorbutan, besonders gut bewährt.It has now been found that cyclic urethanes can be obtained in good yield obtained when one mole of phosgene to about 3 moles of an amino alcohol in organic Solvents in which the amino alcohols and the cyclic urethanes that are formed good, on the other hand the hydrochlorides of the amino alcohols are sparingly soluble without additives allows other acid-binding substances to act; as a solvent have turned out to be next other chlorinated hydrocarbons, e.g. B. chloroform and i, 4-dichlorobutane, especially well proven.
Bei dieser Arbeitsweise wirken die im ÜberschuB vorhandenen Aminoalkohole als säurebindende Mittel, und es scheiden sich pro Möl gebildetes cyclisches Urethan 2 Mol Hydrochlorid des Aminoalkohols ab. Die Umsetzung verläuft am besten bei gewöhnlicher Temperatur, z. B. bei io bis 30°.The amino alcohols present in excess act in this way of working as acid-binding agents, and cyclic urethane formed per oil separates 2 moles of the hydrochloride of the amino alcohol. The implementation works best with ordinary Temperature, e.g. B. at io to 30 °.
Die cyclischen Urethane lassen sich sehr leicht isolieren, indem man nach Beendigung der Umsetzung vom salzsauren Salz trennt, das Lösungsmittel abdestilliert und das cyclische Urethan als Rückstand gewinnt. Aus den salzsauren Salzen lassen sich in bekannter Weise die Aminoalkohole zurückgewinnen. Die Herstellung von Oxazolidon-(2) durch Umsetzung von in Chloroform gelöstem Monoäthanolamin mit Phosgen bei Anwesenheit von Bleicarbonat ist bekannt. Gegenüber dieser Arbeitsweise zeichnet sich das vorliegende Verfahren dadurch aus, daß die Aminoalkohole in den organischen Lösungsmitteln mit Phosgen ohne Zusatz von sonstigen säurebindenden Stoffen umgesetzt werden. Ein solches Verfahren ist aber vorteilhaft, weil sich die mit dem Oxazolidon-(2) bildenden Hydrochloride von Aminoalkoholen im Gegensatz zu Bleichlorid in einfacher Weise durch Zugabe von Alkali- oder Erdalkalihydroxyden in die Ausgangsstoffe zurückverwandeln lassen.The cyclic urethanes can be isolated very easily by when the reaction is complete, it is separated from the hydrochloric acid salt and the solvent is distilled off and the cyclic urethane recovered as a residue. Let out of the hydrochloric acid salts recover the amino alcohols in a known manner. The production of oxazolidone- (2) by reacting monoethanolamine dissolved in chloroform with Phosgene in the presence of lead carbonate is known. Compared to this way of working The present process is characterized in that the amino alcohols in the organic solvents with phosgene without the addition of other acid-binding agents Substances are implemented. However, such a procedure is advantageous because in contrast to the hydrochlorides of amino alcohols which form with the oxazolidone (2) to lead chloride in a simple manner by adding alkali or alkaline earth metal hydroxides can be converted back into the starting materials.
Beispiel In ein Gemisch von 122 Teilen Monoäthanolamin und 488 Teilen Chloroform wird bei io° Phosgen bis zur sauren Reaktion eingeleitet. Das Zusammenballen des sich absondernden Äthanolaminhydrochlorids wird durch kräftiges Rühren verhindert. Nach Beendigung der Umsetzung wird das überschüssige Phosgen mit Luft ausgeblasen, das Reaktionsgemisch abfiltriert und das auf dem Filter zurückbleibende Hydrochlorid des Äthanolamins mit Chloroform nachgewaschen. Das klare Filtrat wird destilliert, wobei Chloroform übergeht und als Rückstand 51,6 Teile Oxazolidon-(2) (F. = 8g°) zurückbleiben-Example In a mixture of 122 parts of monoethanolamine and 488 parts Chloroform is passed in at 10 ° phosgene until an acidic reaction. The clumping The ethanolamine hydrochloride which separates is prevented by vigorous stirring. After the reaction has ended, the excess phosgene is blown out with air, the reaction mixture is filtered off and the hydrochloride remaining on the filter of the ethanolamine was washed with chloroform. The clear filtrate is distilled, with chloroform passing over and 51.6 parts of oxazolidone- (2) (F. = 8g °) as residue stay behind-
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB13985A DE917972C (en) | 1951-03-02 | 1951-03-02 | Process for the manufacture of cyclic urethanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB13985A DE917972C (en) | 1951-03-02 | 1951-03-02 | Process for the manufacture of cyclic urethanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE917972C true DE917972C (en) | 1954-09-16 |
Family
ID=6957795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB13985A Expired DE917972C (en) | 1951-03-02 | 1951-03-02 | Process for the manufacture of cyclic urethanes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE917972C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1152417B (en) * | 1957-08-28 | 1963-08-08 | Robins Co Inc A H | Process for the preparation of 5- (o-alkoxyphenoxymethyl) -oxazolidonen- (2) |
| DE1163328B (en) * | 1959-06-19 | 1964-02-20 | Robins Company Inc H | Process for the preparation of 5-phenoxymethyl-oxazolidonen- (2) |
| DE1198368B (en) * | 1959-08-06 | 1965-08-12 | Robins Co Inc A H | Process for the preparation of 5- (2, 6-dimethoxyphenoxymethyl) -oxazolidone- (2) |
| EP0244810A1 (en) * | 1986-05-06 | 1987-11-11 | MITSUI TOATSU CHEMICALS, Inc. | Process for producing 2-oxazolidinones |
| US4918186A (en) * | 1986-05-06 | 1990-04-17 | Mitsui Toatsu Chemicals, Inc. | Process for producing cyclic ureas |
-
1951
- 1951-03-02 DE DEB13985A patent/DE917972C/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1152417B (en) * | 1957-08-28 | 1963-08-08 | Robins Co Inc A H | Process for the preparation of 5- (o-alkoxyphenoxymethyl) -oxazolidonen- (2) |
| DE1163328B (en) * | 1959-06-19 | 1964-02-20 | Robins Company Inc H | Process for the preparation of 5-phenoxymethyl-oxazolidonen- (2) |
| DE1198368B (en) * | 1959-08-06 | 1965-08-12 | Robins Co Inc A H | Process for the preparation of 5- (2, 6-dimethoxyphenoxymethyl) -oxazolidone- (2) |
| EP0244810A1 (en) * | 1986-05-06 | 1987-11-11 | MITSUI TOATSU CHEMICALS, Inc. | Process for producing 2-oxazolidinones |
| US4918186A (en) * | 1986-05-06 | 1990-04-17 | Mitsui Toatsu Chemicals, Inc. | Process for producing cyclic ureas |
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