SU682525A1 - Method of the preparation of 1,4,2-oxazaphosphorinane - Google Patents
Method of the preparation of 1,4,2-oxazaphosphorinaneInfo
- Publication number
- SU682525A1 SU682525A1 SU762390611A SU2390611A SU682525A1 SU 682525 A1 SU682525 A1 SU 682525A1 SU 762390611 A SU762390611 A SU 762390611A SU 2390611 A SU2390611 A SU 2390611A SU 682525 A1 SU682525 A1 SU 682525A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- preparation
- oxazaphosphorinan
- oxazaphosphorinane
- yield
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 8
- GTWDEUYNZRXMAR-UHFFFAOYSA-N 1,4,2-oxazaphosphinane Chemical compound C1COPCN1 GTWDEUYNZRXMAR-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000047 product Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- -1 dichlorophosphoric acid ester Chemical class 0.000 description 3
- OPROPKSUNRYUKN-UHFFFAOYSA-N 1,3,2-oxazaphospholidine Chemical class C1COPN1 OPROPKSUNRYUKN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
Description
Изобретение относитс к химии фосфорорганических гетероциклических соединений с С-Р-св зью, а именно к новому способу получени производных 1,4,2-оксазафосфоринана общей формулы R R I i CH-N О СЫ где X - алкил или алкоксил; R - водород или низший алкил; R - низший алкил, которые могут найти применение в качестве полупродуктов или физиологически активных соединений. Известен способ получени гетероциклических соединений, содержаш.их в цикле фосфор и азот, взаимодействием эфира дихлорфосфорной кислоты с избытком этилендиамина при 0°С 1. Наиболее близким к предлагаемому по технической сун ности и достигаемому результату в.т етс способ получени производных 1,4,2-оксазафосфоринана взаимодействием 1,3,2-оксазафосфоланов с алифатическими альдегидами при 130-140°С. Выход продуктов составл ет 32-50% 2. К недостаткам этого способа следует отнести сравнительную труднодостунность исходных 1,3,2-оксазафосфоланов, многостадийность их получени , необходимость проведени процесса получени целевых продуктов при высокой температуре, а также невысокий выход производных 1,4,2-оксазафосфоринана . Цель изобретени - упрощение процесса и повышение выхода целевых продуктов. Это достигаетс предлагаемым способом получени производных 1,4,2-оксазафосфоринана , который заключаетс в том, что полный эфир фосфористой или фосфонистой кислоты подвергают взаимодействию при нагревании до 70-100°С с продуктом конденсации алкил-р-оксиэтиламина, альдегида и спирта. Отличительным признаком способа вл етс использование в качестве эфира кислоты фосфора полного эфира фосфористой или фосфонистой кислоты, которые подвергают взаимодействию с продуктом конденсации алкил-р-оксиэтиламина, альдегида и спирта в вышеописанных услови х. Способ характеризуетс простотой, позвол ет использовать доступные реагенты и повышает выход целевых продуктов до 72-77%. Пример 1. 2-Оксо-2-этокси-4-метил1 ,4,2-оксазафосфоринан.This invention relates to the chemistry of organophosphorus heterocyclic compounds with a C-P bond, in particular to a new method for the preparation of 1,4,2-oxazaphosphorinan derivatives of the general formula R I i CH-N O C where X is alkyl or alkoxy; R is hydrogen or lower alkyl; R is lower alkyl, which can be used as intermediates or physiologically active compounds. There is a known method for producing heterocyclic compounds containing phosphorus and nitrogen in the cycle, by reacting dichlorophosphoric acid ester with an excess of ethylene diamine at 0 ° C. 1. The closest to the proposed technical technical result and the result obtained is 1.4 2-oxazaphosphorinan by the interaction of 1,3,2-oxazaphospholanes with aliphatic aldehydes at 130-140 ° C. The yield of products is 32-50% 2. The disadvantages of this method include the comparative hardness of the initial 1,3,2-oxazaphospholanes, the multistage production, the need to carry out the process of obtaining the desired products at high temperature, and the low yield of derivatives 1,4, 2-oxazaphosphorinan. The purpose of the invention is to simplify the process and increase the yield of the target products. This is achieved by the inventive method for the preparation of 1,4,2-oxazaphosphorinan derivatives, which consists in reacting the complete ester of phosphorous or phosphonic acid when heated to 70-100 ° C with the condensation product of alkyl-p-hydroxyethylamine, aldehyde and alcohol. A distinctive feature of the process is the use of a complete phosphorous or phosphonic acid ester as the phosphoric acid ester, which reacts with the condensation product of alkyl-p-hydroxyethylamine, aldehyde and alcohol under the conditions described above. The method is characterized by simplicity, allows the use of available reagents and increases the yield of the target products to 72-77%. Example 1. 2-Oxo-2-ethoxy-4-methyl1, 4,2-oxazaphosphorinan.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU762390611A SU682525A1 (en) | 1976-07-28 | 1976-07-28 | Method of the preparation of 1,4,2-oxazaphosphorinane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU762390611A SU682525A1 (en) | 1976-07-28 | 1976-07-28 | Method of the preparation of 1,4,2-oxazaphosphorinane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU682525A1 true SU682525A1 (en) | 1979-08-30 |
Family
ID=20672063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762390611A SU682525A1 (en) | 1976-07-28 | 1976-07-28 | Method of the preparation of 1,4,2-oxazaphosphorinane |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU682525A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4977292A (en) * | 1989-12-15 | 1990-12-11 | W. R. Grace & Co.-Conn. | 4-phosphonomethyl-2-hydroxy-2-oxo-1,4,2-oxazaphosphorinane N-oxide and water-soluble salts thereof |
| RU2605556C1 (en) * | 2015-12-03 | 2016-12-20 | Федеральное Государственное Унитарное Предприятие "Государственный Ордена Трудового Красного Знамени Научно-Исследовательский Институт Химических Реактивов И Особо Чистых Химических Веществ" | 4-n-[(dihydroxyphosphoryl)methyl]-6-(chloromethyl)-1,4,2-oxazaphosphorinane and method for production thereof |
-
1976
- 1976-07-28 SU SU762390611A patent/SU682525A1/en active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4977292A (en) * | 1989-12-15 | 1990-12-11 | W. R. Grace & Co.-Conn. | 4-phosphonomethyl-2-hydroxy-2-oxo-1,4,2-oxazaphosphorinane N-oxide and water-soluble salts thereof |
| RU2605556C1 (en) * | 2015-12-03 | 2016-12-20 | Федеральное Государственное Унитарное Предприятие "Государственный Ордена Трудового Красного Знамени Научно-Исследовательский Институт Химических Реактивов И Особо Чистых Химических Веществ" | 4-n-[(dihydroxyphosphoryl)methyl]-6-(chloromethyl)-1,4,2-oxazaphosphorinane and method for production thereof |
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