SU137925A1 - Method for producing alkyl esters of 2, 4-dinitrothiophenol - Google Patents
Method for producing alkyl esters of 2, 4-dinitrothiophenolInfo
- Publication number
- SU137925A1 SU137925A1 SU671290A SU671290A SU137925A1 SU 137925 A1 SU137925 A1 SU 137925A1 SU 671290 A SU671290 A SU 671290A SU 671290 A SU671290 A SU 671290A SU 137925 A1 SU137925 A1 SU 137925A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dinitrothiophenol
- alkyl esters
- producing alkyl
- solution
- potassium
- Prior art date
Links
- MHKRINONGZJSSL-UHFFFAOYSA-N 2,4-dinitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC=C(S)C([N+]([O-])=O)=C1 MHKRINONGZJSSL-UHFFFAOYSA-N 0.000 title description 2
- 125000005907 alkyl ester group Chemical group 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 6
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 4
- -1 2,4-dinitrothiophenol alkyl ethers Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- ZFEFQDSXWYVVLS-UHFFFAOYSA-N 2,3-dinitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC=CC(S)=C1[N+]([O-])=O ZFEFQDSXWYVVLS-UHFFFAOYSA-N 0.000 description 2
- CVYZVNVPQRKDLW-UHFFFAOYSA-N 2,4-dinitroanisole Chemical compound COC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O CVYZVNVPQRKDLW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001351 alkyl iodides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- JKIFPWHZEZQCQA-UHFFFAOYSA-N 2-nitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC=CC=C1S JKIFPWHZEZQCQA-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- CSABAZBYIWDIDE-UHFFFAOYSA-N sulfino hydrogen sulfite Chemical class OS(=O)OS(O)=O CSABAZBYIWDIDE-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Изьестен способ получени алкильных эфиров 2,4-динитротиофенола , основанный на взаимодействии 2,4-динитрохлорбензола с гидросульфидом кали и последующем кип чени:; полученного нитротиофенола с спиртовым раствором едкого кали и йодистого алкила. При этом в качестве побочных продуктов реакции получают тетранитродифенилсульфид и тетраиитродифенилдисульфид.A process for the preparation of 2,4-dinitrothiophenol alkyl ethers based on the interaction of 2,4-dinitrochlorobenzene with potassium hydrosulfide and subsequent boiling is iestien ;; nitrothiophenol obtained with an alcohol solution of potassium hydroxide and alkyl iodide. In addition, tetranitrodiphenylsulfide and tetraitrodiphenyl disulfide are obtained as side reaction products.
Предлагаемый способ по г|гучени алкильных эфиров 2,4-динитротиофенола основан на реакции 2,4-динитроанизола с гидросульфидом кали и последующем взаимодействии полученного таким способом динитротиофенола с йодистым алдилом. Реакцию ведут в растворе спиртовой щелочи при комнатной температуре, при этом м гкие услови реакции и характер реагентов исключают возможность образовани побочных продуктов.The proposed method for the treatment of 2,4-dinitrothiophenol alkyl esters is based on the reaction of 2,4-dinitroanisole with potassium hydrosulfide and the subsequent interaction of dinitrothiophenol obtained in this way with aldyl iodide. The reaction is carried out in a solution of alcoholic alkali at room temperature, while the mild reaction conditions and the nature of the reagents exclude the possibility of the formation of by-products.
Пример. 0,0025 г-мол 2,4-дипитроанизола при нагревании раствор ют в 25 мл этилового спирта и после охлаждени к полученному раствору приливают раствор 0,002 г-люл едкого кали в 5 мл этилового спирта. Через 15 мин к раствору прибавл ют 0,007 г-мол гидросульфида кали в 16 мл спиртового раствора и оставл ют реакционную смесь сто ть на два часа, при этом светлокрасна окраска раствора переходит в темнокоричневую. По истечении двух часов к реакционной смеси прибавл ют еще 0,004 г-мол едкого кали в 5 мл этилового спирта и 0,007 г-мол йодистого метила. После часовой выдержки раствор разбавл ют водой, эфир отсасывают и перекристаллизовывают из этилового спирта и лигроина. Выход метилового эфира динитротиофенола (т. пл. 126°) составл ет 87% от теоретического.Example. 0.0025 gmol of 2,4-dipitroanisole is dissolved in 25 ml of ethanol when heated and, after cooling, a solution of 0.002 g of potassium hydroxide in 5 ml of ethanol is added to the resulting solution. After 15 minutes, 0.007 gmol of potassium hydrosulfide in 16 ml of an alcoholic solution was added to the solution and the reaction mixture was left to stand for two hours, while the bright red color of the solution turned dark brown. After two hours, another 0.004 gm mol of potassium hydroxide in 5 ml of ethyl alcohol and 0.007 gm mol of methyl iodide are added to the reaction mixture. After an hour's exposure, the solution is diluted with water, the ether is filtered off with suction and recrystallized from ethyl alcohol and ligroin. The yield of dinitrothiophenol methyl ester (mp 126 °) is 87% of the theoretical.
Аналогичным способом получены этиловый, н-нропиловый, н-бутиловый , и-бутиловый, н-амиловый и ы-амиловый эфиры динитротиофенола. Выход эфиров в зависимости от характера алкильной группы колеблетс от 40 до 87%.The ethyl, n-nropyl, n-butyl, and-butyl, n-amyl and s-amyl esters of dinitrothiophenol are obtained in a similar way. The yield of the esters, depending on the nature of the alkyl group, ranges from 40 to 87%.
137925- 2 Предмет изобретени 137925- 2 Subject of the invention
Способ получени алкильных эфиров 2,4-динитротиофепола, отли чающийс тем, что, с целью исключени образовани побочных моно- и дисульфитов замещенного фенола, в качестве исходного продукта используют 2,4-динитроанизол, который последовательно обрабатывают алкогол том кали и гидросульфидом кали с последующим алк.илиро,ванием на холоду с помощью йодистого алкила.The method of producing alkyl ethers of 2,4-dinitrothiophenol, which is distinguished by the fact that, in order to eliminate the formation of substituted mono- and disulfites of substituted phenol, 2,4-dinitroanisol is used as a starting product, which is successively treated with potassium alcohol and potassium hydrogen sulfide, followed by alk.ilirovanie in the cold with alkyl iodide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU671290A SU137925A1 (en) | 1960-06-23 | 1960-06-23 | Method for producing alkyl esters of 2, 4-dinitrothiophenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU671290A SU137925A1 (en) | 1960-06-23 | 1960-06-23 | Method for producing alkyl esters of 2, 4-dinitrothiophenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU137925A1 true SU137925A1 (en) | 1960-11-30 |
Family
ID=48294106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU671290A SU137925A1 (en) | 1960-06-23 | 1960-06-23 | Method for producing alkyl esters of 2, 4-dinitrothiophenol |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU137925A1 (en) |
-
1960
- 1960-06-23 SU SU671290A patent/SU137925A1/en active
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