SU255943A1 - METHOD OF OBTAINING N-ALKYL-2-OKCIMETHYL-HEXAMETHYLENEIMINES - Google Patents
METHOD OF OBTAINING N-ALKYL-2-OKCIMETHYL-HEXAMETHYLENEIMINESInfo
- Publication number
- SU255943A1 SU255943A1 SU1244180A SU1244180A SU255943A1 SU 255943 A1 SU255943 A1 SU 255943A1 SU 1244180 A SU1244180 A SU 1244180A SU 1244180 A SU1244180 A SU 1244180A SU 255943 A1 SU255943 A1 SU 255943A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- acid
- okcimethyl
- hexamethyleneimines
- obtaining
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000007126 N-alkylation reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- -1 aromatic sulfonic acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- QYJXDIUNDMRLAO-UHFFFAOYSA-N butyl 4-methylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=C(C)C=C1 QYJXDIUNDMRLAO-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 1
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
Изобретение относитс к классу тетероциклических соединений с одним атомом азота. Полученные соединени в литературе не описаны , они могут найти применение в качестве физиологически активных веществ.The invention relates to the class of tetrocyclic compounds with a single nitrogen atom. The compounds obtained are not described in the literature; they can be used as physiologically active substances.
Предложен способ получени К-алкил-2-оксиметилгексаметилениминов , заключающийс в том, что эфиры гексаметилениминкарбоновой-2 кислоты алкилнруют эфирами серной кислоты или ароматических сульфокислот, или ацилируют до соответствующих N-алкилили N-ацилзамещенных, которые восстанавливают алюмогидридом лити до соответствующего ами«оспирта. Целевой продукт выдел ют известным способом.A method for the preparation of K-alkyl-2-hydroxymethylhexamethylenimines is proposed. It consists in that the esters of hexamethyleniminecarboxylic-2 acid are alkylated with ethers of sulfuric acid or aromatic sulfonic acids, or are acylated to the corresponding N-alkylation of N-acylsubstituted alcohols, which are brought to the N-alkylation of the N-alkylamino-N-alkylamino esters, which are given to the N-alkylamino esters, which are brought to the N-alkylamino esters, which are brought to the N-alkylation of the N-alkylamino-2-N-alkyl-N-alkyl acids, which are brought up with the esters of sulfuric acid or aromatic sulfonic acids. The desired product is isolated in a known manner.
Пример 1. Получение М-этил-2-Ъксиметил-гексаметиленимина .Example 1. The preparation of M-ethyl-2-xymethyl-hexamethylenimine.
Раствор 17,1 г этилового эфира гексаметилениминкарбоновой-2 кислоты и 19,9 г этилового эфира г-толуолсульфокислоты в 200 мл ксилола нагревают при кипении 15 час. Раствор экстрагируют разбавленной сол ной кислотой (1:1), кислые экстракты объедин ют, при охлаждении подщелачивают 20%-ным едким натром и основани извлекают эфиром. После высушивани «ад сульфатом магни растворитель упаривают, остаток перегон ют в вакууме. Получают 11,5 г (58%) этилового эфира N-этилгексаметилениминкарбоновой-2 кислоты с т. кип. 70-72°С (2 мм рт. ст), п2 1,4542.A solution of 17.1 g of ethyl hexamethyleneiminecarboxylic acid-2 and 19.9 g of ethyl g-toluenesulfonic acid in 200 ml of xylene is heated at boiling for 15 hours. The solution is extracted with diluted hydrochloric acid (1: 1), the acidic extracts are combined, basified with cooling with alkaline 20% sodium hydroxide and the bases removed with ether. After drying, the "adduct with magnesium sulfate is evaporated and the residue is distilled in vacuo. Obtain 11.5 g (58%) of ethyl ester of N-ethylhexamethyleneiminecarboxylic-2 acid with so Kip. 70-72 ° С (2 mm of mercury), p2 1.4542.
Найдено, С 66,35, 66,13; Н 10,65, 10,39.Found: C, 66.35, 66.13; H 10.65, 10.39.
CaHaiNO.CaHaiNO.
Вычислено, %: С 66,29; Н 10,62.Calculated,%: C, 66.29; H 10.62.
К 1,14 г алюмогидрида лити в 50 мл сухого эфира за 0,5 час приливают по капл м раствор 5,97 г этилового эфира N-этилгексаметилениминкар боновой-2 кислоты в 50 мл эфира. На следующий день реакционную смесь разлагают последовательным нрибавлением 1,9 мл воды, 1,7 мл 20%-ного едкого натра, 4.1 ли воды и 5,6 мл 40J/o-Horo едкого натра. Эфирный раствор декантируют, осадок экстрагируют гор чим эфиром. Эфир испар ют, остаток перегон ют. Выход 3,4 г (79%), т. кип. 73-74°С (2,5 мм рт. ст), п§ 1,4770, df 0,9501, MR: найдено 46,77, вычислено 47,08.To 1.14 g of lithium aluminum hydride in 50 ml of dry ether over 0.5 hour, a solution of 5.97 g of ethyl ester of N-ethylhexamethyleneimcarcarboxylic acid in 50 ml of ether is added dropwise. The next day, the reaction mixture was decomposed by successively sprinkling 1.9 ml of water, 1.7 ml of 20% sodium hydroxide, 4.1 li of water, and 5.6 ml of 40J / o-Horo sodium hydroxide. The ether solution is decanted, the precipitate is extracted with hot ether. The ether is evaporated, the residue is distilled. The yield of 3.4 g (79%), t. Kip. 73-74 ° C (2.5 mmHg), P. 1.4770, df 0.9501, MR: found 46.77, 47.08 were calculated.
Найдено, о/о: С 68,77, 68.99; Н 12,18, 12,22.Found, o / o: C 68.77, 68.99; H 12.18, 12.22.
C,Hi9NO.C, Hi9NO.
Вычислено, о/о: С 68,74: Н 12,18.Calculated, o / o: C 68.74: H 12.18.
Пример 2. Получение Н-бутил-2-оксиметилгексаметиленимина .Example 2 Preparation of H-butyl-2-hydroxymethylhexamethyleneimine
Раствор 1,71 г этилового эфира гексаметилениминкарбоновой-2 кислоты и 2,28 г бутилового эфира п-толуолсульфокислоты в 50 мл су.хого ксилола нагревают при кипении 10 час.A solution of 1.71 g of ethyl 2-ester of hexamethyleneimocarboxylic acid and 2.28 g of p-toluenesulfonic acid butyl ester in 50 ml of dry xylene is heated at boiling point for 10 hours.
Publications (1)
| Publication Number | Publication Date |
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| SU255943A1 true SU255943A1 (en) |
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