SU302337A1 - WAY OF OBTAINING 3- (PHENIL - \, \ - DIALKYLSULFAMIDO) -1-ACETOXYBUTANE - Google Patents
WAY OF OBTAINING 3- (PHENIL - \, \ - DIALKYLSULFAMIDO) -1-ACETOXYBUTANEInfo
- Publication number
- SU302337A1 SU302337A1 SU1399920A SU1399920A SU302337A1 SU 302337 A1 SU302337 A1 SU 302337A1 SU 1399920 A SU1399920 A SU 1399920A SU 1399920 A SU1399920 A SU 1399920A SU 302337 A1 SU302337 A1 SU 302337A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acetoxybutane
- dialkylsulfamido
- obtaining
- phenil
- way
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 5
- CSKNSYBAZOQPLR-UHFFFAOYSA-N Benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005265 dialkylamine group Chemical group 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N Dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- -1 bromomethylbenzene sulfamide Chemical compound 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ZASWJUOMEGBQCQ-UHFFFAOYSA-L dibromolead Chemical compound Br[Pb]Br ZASWJUOMEGBQCQ-UHFFFAOYSA-L 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к способу получени производных и-сульфамидобензилового спирта , которые могут найти применение в качестве лечебных препаратов.The invention relates to a process for the preparation of sulphamidobenzyl alcohol derivatives, which can be used as therapeutic preparations.
Известен способ получени соединени формулыA known method for producing a compound of the formula
-SO NCCaHi),-SO NCCaHi),
CHgCOOCHjCHgCOOCHj
взаимодействием бромметилбензолсульфамида с дипропиламином в растворе ацетона при 10°С, полученный при этом М,М-дипропил-/гбромметилбензолсульфамид раствор ют в уксусной кислоте и добавл ют РЬО. Реакционную массу выдерживают в течение трех дней, затем отфильтровывают бромистый свинец, отгон ют уксусную кислоту, остаток экстрагируют эфиром, сушат эфирный раствор сульфатом магни , отгон ют эфир и целевой продукт выдел ют вакуумной разгонкой. Однако способ многостадиен, выход целевого продукта небольшой, процесс продолжителен.by reacting bromomethylbenzene sulfamide with dipropylamine in an acetone solution at 10 ° C, the M, M-dipropyl- / gbromomethylbenzenesulfamide thus obtained is dissolved in acetic acid and PbO is added. The reaction mass is maintained for three days, then lead bromide is filtered off, acetic acid is distilled off, the residue is extracted with ether, the ether solution is dried with magnesium sulfate, the ether is distilled off and the target product is isolated by vacuum distillation. However, the multi-stage method, the yield of the target product is small, the process is long.
С целью упрощени процесса и увеличени выхода целевого продукта, предлагаетс 3-(фенилсульфохлорид)-1-ацетоксибутан подвергать взаимодействию с диалкиламином при О-10°С в среде органического растворител с последующим выделением целевого продукта известным способом. Выход 60-90%.In order to simplify the process and increase the yield of the target product, 3- (phenylsulfonyl chloride) -1-acetoxybutane is proposed to be reacted with dialkylamine at O-10 ° C in an organic solvent medium, followed by isolation of the target product in a known manner. Yield 60-90%.
Пример. В четырехгорлую колбу, снабженную механической мешалкой, обратным холодильником, термометром и капельной воронкой , помещают 10 г 3-(фенилсульфохлорид )-1-ацетоксибутана, растворенного в 40 мл ацетона. Температуру довод т до 10°С. К реакционной массе при перемешивании по капл м добавл ют раствор 5 г диэтиламина в 15 мл ацетона. Перемешивание продолжаютExample. In a four-necked flask equipped with a mechanical stirrer, a reflux condenser, a thermometer and a dropping funnel, 10 g of 3- (phenylsulfonyl chloride) -1-acetoxybutane dissolved in 40 ml of acetone are placed. The temperature is adjusted to 10 ° C. Under stirring, a solution of 5 g of diethylamine in 15 ml of acetone is added dropwise to the reaction mass. Stirring is continued.
еще 2-3 час (10°С). Выпавшие кристаллы отфильтровывают , фильтрат упаривают при пониженном давлении, раствор ют в эфире и тщательно промывают водой, сушат над Na2SO4, упаривают, остаток перегон ют в вакууме . Получают продукт с т. кип. ,5-another 2-3 hours (10 ° C). The precipitated crystals are filtered off, the filtrate is evaporated under reduced pressure, dissolved in ether and washed thoroughly with water, dried over Na2SO4, evaporated, the residue is distilled in vacuo. Get the product with m. Kip. ,five-
1 ММ рт. ст.; п 1,5125, который соответствует соединению1 mmHg v .; P 1,5125, which corresponds to the connection
СНз-СН-СНг-СНгОСОСНз СНз-СН-СНг-СНгОСОСНз
(СгН5),(CrH5),
В услови х, аналогичных услови м получени З-(фенилсульфамидо) - 1-ацетоксибутана, путем взаимодействи 1 г-моль 3-(фенилсульфохлорид )-1-ацетоксибутана с 2 г-моль диметиламина получают 3-(фенил-Х,М-диметилсульфамид )-1-ацетоксибутан с выходом 57,8%; т. кип. 171°С/0,5-1 мм рт. ст., 1,5200; df 1,1678.Under conditions similar to those for the preparation of 3- (phenylsulfonamide) -1-acetoxybutane, by reacting 1 g-mole of 3- (phenylsulfonyl chloride) -1-acetoxybutane with 2 g-mole of dimethylamine, 3- (phenyl-X, M-dimethylsulfamide A) -1-acetoxybutan with a yield of 57.8%; m.p. 171 ° C / 0.5-1 mm Hg Art., 1,5200; df 1.1678.
Найдено, %: S 10,78; 10,70; N 4,57; 4,80.Found,%: S 10.78; 10.70; N 4.57; 4.80.
Вычислено, %: S 10,70; N 4,68.5Calculated,%: S 10.70; N 4.68.5
Предмет изобретени Subject invention
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU302337A1 true SU302337A1 (en) |
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