PL409030A1 - Method for producing 1,3-bis(2-hydroxyalkyl)-6-methyluracil - Google Patents
Method for producing 1,3-bis(2-hydroxyalkyl)-6-methyluracilInfo
- Publication number
- PL409030A1 PL409030A1 PL409030A PL40903014A PL409030A1 PL 409030 A1 PL409030 A1 PL 409030A1 PL 409030 A PL409030 A PL 409030A PL 40903014 A PL40903014 A PL 40903014A PL 409030 A1 PL409030 A1 PL 409030A1
- Authority
- PL
- Poland
- Prior art keywords
- stage
- solvent
- methyluracil
- catalyst
- reaction
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- SHVCSCWHWMSGTE-UHFFFAOYSA-N 6-methyluracil Chemical compound CC1=CC(=O)NC(=O)N1 SHVCSCWHWMSGTE-UHFFFAOYSA-N 0.000 abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002924 oxiranes Chemical class 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Landscapes
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Sposób dotyczy wytwarzania związku o wzorze 1, gdzie R oznacza odpowiednio atom wodoru -H albo grupę metylową -CH3, w reakcjach 6-metylouracylu o wzorze 2 z oksiranami o wzorze 3 w postaci odpowiednio tlenku etylenu dla R = -H lub tlenku propylenu dla R = -CH3. W pierwszym etapie prowadzi się reakcje w reaktorkach ciśnieniowych, przy stosunku molowym 6-metylouracylu do oksiranu równym 1 : 2, w rozpuszczalniku w obecności trietyloaminy jako katalizatora, zaś w drugim etapie po zakończeniu reakcji oddestylowuje się pod zmniejszonym ciśnieniem katalizator i rozpuszczalnik, po czym dodaje się metanol i odsącza otrzymany związek, który następnie krystalizuje się z etanolu. W pierwszym etapie, w przypadku tlenku etylenu reakcję prowadzi się w temperaturze 50 ÷ 60°C przez co najmniej 36 godzin, zaś w przypadku tlenku propylenu w temperaturze 60 ÷ 70°C przez co najmniej 36 godzin. Ponadto w pierwszym etapie jako rozpuszczalnik stosuje się sulfotlenek dimetylu, zaś w drugim etapie oddestylowanie katalizatora i rozpuszczalnika prowadzi się pod ciśnieniem mniejszym od 1 kPa. Wynalazek znajduje zastosowanie do otrzymywania liniowych poliuretanów, poliestrów oraz jako potencjalny związek wyjściowy w syntezie leków.The method relates to the preparation of a compound of formula 1, wherein R is a hydrogen atom -H or a methyl group -CH3, respectively, by reaction of 6-methyluracil of formula 2 with oxiranes of formula 3 in the form of ethylene oxide for R = -H or propylene oxide for R, respectively = -CH3. In the first stage, reactions are carried out in pressure reactors, with a molar ratio of 6-methyluracil to oxirane of 1: 2, in a solvent in the presence of triethylamine as a catalyst, and in the second stage after completion of the reaction, the catalyst and solvent are distilled off under reduced pressure, and then added methanol and the resulting compound is filtered off, which is then crystallized from ethanol. In the first stage, in the case of ethylene oxide, the reaction is carried out at a temperature of 50 to 60 ° C for at least 36 hours, and in the case of propylene oxide at a temperature of 60 to 70 ° C for at least 36 hours. In addition, dimethyl sulfoxide is used as the solvent in the first stage, and the catalyst and solvent are distilled off in the second stage at a pressure less than 1 kPa. The invention finds application in the preparation of linear polyurethanes, polyesters and as a potential starting compound in the synthesis of drugs.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL409030A PL228504B1 (en) | 2014-07-30 | 2014-07-30 | Method for producing 1,3-bis(2-hydroxyalkyl)-6-methyluracil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL409030A PL228504B1 (en) | 2014-07-30 | 2014-07-30 | Method for producing 1,3-bis(2-hydroxyalkyl)-6-methyluracil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL409030A1 true PL409030A1 (en) | 2016-02-01 |
| PL228504B1 PL228504B1 (en) | 2018-04-30 |
Family
ID=55178453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL409030A PL228504B1 (en) | 2014-07-30 | 2014-07-30 | Method for producing 1,3-bis(2-hydroxyalkyl)-6-methyluracil |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL228504B1 (en) |
-
2014
- 2014-07-30 PL PL409030A patent/PL228504B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL228504B1 (en) | 2018-04-30 |
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