CS240127B1 - Method of 1,2-benzoxazolone preparation - Google Patents
Method of 1,2-benzoxazolone preparation Download PDFInfo
- Publication number
- CS240127B1 CS240127B1 CS846646A CS664684A CS240127B1 CS 240127 B1 CS240127 B1 CS 240127B1 CS 846646 A CS846646 A CS 846646A CS 664684 A CS664684 A CS 664684A CS 240127 B1 CS240127 B1 CS 240127B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- aminophenol
- benzoxazolone
- urea
- preparation
- temperature
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- QLDQYRDCPNBPII-UHFFFAOYSA-N 1,2-benzoxazol-3-one Chemical compound C1=CC=C2C(O)=NOC2=C1 QLDQYRDCPNBPII-UHFFFAOYSA-N 0.000 title claims description 5
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims abstract description 32
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000004202 carbamide Substances 0.000 claims abstract description 10
- 238000009833 condensation Methods 0.000 claims abstract description 5
- 230000005494 condensation Effects 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 239000011541 reaction mixture Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract 1
- -1 urea o-aminophenol Chemical compound 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- KLQYKJMMAPSQCP-UHFFFAOYSA-N methyl 1-benzyl-4-methylpyrrolidine-3-carboxylate Chemical compound C1C(C)C(C(=O)OC)CN1CC1=CC=CC=C1 KLQYKJMMAPSQCP-UHFFFAOYSA-N 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Způsob přípravy benzoxazolonu kondenzací o-aminofenolu s močovinou, jehož podstata spočívá v tom, že se do roztavené močoviny dávkuje o-aminofenol s obsahem vody 5 až 50 Vo hmotnostních, při molárním poměru močovina-o-aminofenol 1 až 1,1 :1, načež se reakční směs vyhřeje na teplotu 200 až 250 °C a tato teplota se udržuje do skončení reakce.Process for preparing benzoxazolone by condensation o-aminophenol with urea, the nature of which it consists in getting into the molten urea o-aminophenol containing water 5 to 50 in weight, at molar a urea-o-aminophenol ratio of 1 to 1.1: 1, then the reaction mixture is heated to a temperature 200 to 250 ° C and this temperature is maintained until end of the reaction.
Description
Vynález se týká způscbv přípravy 1,2-benzoxazolonu kondenzací močoviny s 2-aminofenolem.The invention relates to a process for the preparation of 1,2-benzoxazolone by condensation of urea with 2-aminophenol.
1,2-benzoxazolon vzniká podle údajů v literatuře řadou reakcí, vycházejících z derivátů kyseliny salicylové, derivátů benzoxazolu nebo z , 2-aminofenolu. Laboratorní přípravu benzoxazolonu z 2-aminofenolu působením fosgenu v prostředí organických rozpouštědel popisují Chelmicki, Jacoby a Meyer. Tavením 2-aminofenolhydrochloridu s močovinou připravil benzoxaxazolon Sandmeyer. Průmyslová výroba benzoxazolonu reakcí fosgenu s 2-aminofenolem ve vodněalkalickém prostředí je uvedena v reportech o německém chemickém průmyslu. Nevýhodou uváděných postupů přípravy benzoxazolonu z 2-aminofenolu je používání toxického fosgenu nebo nutnost převádění 2-aminofenolu na hydrochlorid, neboť získání suchého 2-aminofenolu bez použití organických rozpouštědel je obtížné vzhledem k tomu, že tato látka při teplotách blízkých 100 °C sublirnuje.According to literature data, 1,2-benzoxazolone is formed by a series of reactions starting from salicylic acid derivatives, benzoxazole derivatives or from 2-aminophenol. Laboratory preparation of benzoxazolone from 2-aminophenol by phosgene treatment in organic solvents is described by Chelmicki, Jacoby and Meyer. Melting 2-aminophenol hydrochloride with urea prepared benzoxaxazolone Sandmeyer. The industrial production of benzoxazolone by the reaction of phosgene with 2-aminophenol in an aqueous-alkaline environment is reported in reports on the German chemical industry. A disadvantage of the present processes for the preparation of benzoxazolone from 2-aminophenol is the use of toxic phosgene or the need to convert 2-aminophenol to the hydrochloride, since it is difficult to obtain dry 2-aminophenol without the use of organic solvents.
Uvedené nevýhody odstraňuje způsob přípravy 1,2-benzoxazolonu kondenzací močoviny s 2-aminofenolem, jehož podstata spočívá v tom, že se do roztavené močoviny dávkuje pasta o-aminofenolu s obsahem vody 5 až 50 % hmot. při molárním poměru až 1,1 molu močoviny na 1 mol o-aminofenolu, reakční směs se vyhřeje na 200 až 250 °C a tato teplota se udržuje až do konce reakce.These disadvantages are overcome by a process for the preparation of 1,2-benzoxazolone by the condensation of urea with 2-aminophenol, which comprises adding o-aminophenol paste with a water content of 5 to 50% by weight in molten urea. at a molar ratio of up to 1.1 mole of urea per mole of o-aminophenol, the reaction mixture is heated to 200-250 ° C and this temperature is maintained until the end of the reaction.
Výhodou postupu podle vynálezu je použití vlhké, nesušené pasty; o-aminofenolu, přičemž výtěžnost reakce je 90 až 95 ·% teorie při obsahu benzoxazolonu v produktu 90 až 95 %. .· . .........An advantage of the process according to the invention is the use of a wet, non-dried paste; o-aminophenol, the reaction yield being 90-95% of the theory with a benzoxazolone content of 90-95%. . ·. .........
Pro bližší objasnění: podstaty vynálezu je uveden příklad provedení:For further explanation: the essence of the invention is an example implementation:
Do 80 g močoviny, roztavené a vyhřáté na teplotu 140 °C se za míchání během 1,5 hodiny dávkuje 136 g o-aminofenolu 100 % ve formě 85% vlhké, látky. Teplota během dávkováni poklesne na 120 °C a udržuje se na této úrovni. Dochází k uvolňování amoniaku. a. vodní,.páry,, které jsou odváděny přes nechlazený zpětný chladič. Po skončeném dávkování se reakční směs vyhřívá během 4 hodin na teplotu 220 °C a při této teplotě se 3 hodiny vymíchává. Po kontrole na vymizení o-aminofenolu (chromatografickyj ,a stanovení teploty tání produktu se tavenina převede na porcelánovou misku, po ztuhnuti a vychladnutí se rozdrtí a rozemele.136 g of o-aminophenol 100% in the form of 85% wet substance are metered in with stirring over 1.5 hours to 80 g of urea, melted and heated to 140 ° C. The temperature drops to 120 ° C during dosing and is maintained at this level. Ammonia is released. and water vapors that are discharged through an uncooled reflux condenser. After the addition was complete, the reaction mixture was heated to 220 ° C for 4 hours and stirred at this temperature for 3 hours. After checking for the disappearance of o-aminophenol (chromatographic, and determining the melting point of the product), the melt is transferred to a porcelain dish, after solidification and cooling, it is crushed and ground.
Získá se 160 g 100 % benzoxazolonu ve formě 95% látky o teplotě tání 138 °C. Výtěžek kondenzace je 95 % teorie, počítáno na výchozí o-aminofenol.160 g of 100% benzoxazolone are obtained in the form of 95% of a melting point of 138 ° C. The yield of condensation is 95% of theory, calculated on the starting o-aminophenol.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS846646A CS240127B1 (en) | 1984-09-04 | 1984-09-04 | Method of 1,2-benzoxazolone preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS846646A CS240127B1 (en) | 1984-09-04 | 1984-09-04 | Method of 1,2-benzoxazolone preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS664684A1 CS664684A1 (en) | 1985-06-13 |
| CS240127B1 true CS240127B1 (en) | 1986-02-13 |
Family
ID=5414014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS846646A CS240127B1 (en) | 1984-09-04 | 1984-09-04 | Method of 1,2-benzoxazolone preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS240127B1 (en) |
-
1984
- 1984-09-04 CS CS846646A patent/CS240127B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS664684A1 (en) | 1985-06-13 |
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