SU165731A1 - Method of producing 2-methylthieno - Google Patents
Method of producing 2-methylthienoInfo
- Publication number
- SU165731A1 SU165731A1 SU813587A SU813587A SU165731A1 SU 165731 A1 SU165731 A1 SU 165731A1 SU 813587 A SU813587 A SU 813587A SU 813587 A SU813587 A SU 813587A SU 165731 A1 SU165731 A1 SU 165731A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methylthieno
- producing
- anhydrous
- hour
- stirring
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- AXZWODMDQAVCJE-UHFFFAOYSA-L Tin(II) chloride Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PJCCSZUMZMCWSX-UHFFFAOYSA-N 4,4-dimethoxybutan-2-one Chemical compound COC(OC)CC(C)=O PJCCSZUMZMCWSX-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- DQANESWWYOCKRW-UHFFFAOYSA-N thieno[3,2-b]thiophen-5-amine Chemical compound S1C=CC2=C1C=C(N)S2 DQANESWWYOCKRW-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Предлагаетс способ получени 2-метилтиено- (2,3-в)-тиено-(2,3-в)- и тиено-(3,2-в)-пиридинов . Эти соединени получают конденсацией двойной олов нной соли хлоргидрата 2аминотиофтена или 2-ам1Инотиено-(3,2-в)-тиофена с диалкилацеталем ацетоацетальдегида в присутствии безводного хлористого цинка нагреванием в растворе абсолютного этилового спирта.A method for the preparation of 2-methylthieno- (2,3-b) -thieno- (2,3-b) - and thieno- (3,2-b) -pyridines is proposed. These compounds are obtained by condensation of the double tin salt of 2-aminothioftene or 2-am1-Enothieno (3,2-b) -thiophene hydrochloride with acetoacetaldehyde dialkyl acetal in the presence of anhydrous zinc chloride by heating in a solution of absolute ethanol.
Полученные соединени могут быть использованы дл получени полиметиновых красителей .The resulting compounds can be used to prepare polymethine dyes.
Пример 1. 2 - мети л тие н о - (2,3 - в) т и е н о- (2,3-в) -п и р и д и н.Example 1. 2 - methyl noth - (2,3 - b) t and e n about - (2,3-b) -n and p and d and n.
К смеси 64,0 г двойной олов нной соли хлоргидрата 2-аминотиофтена (0,1 г-моль), 250,0 мл безводного этанола и 5,0 г безводного плавленого хлористого цинка при 65-75° С и энергичном размешивании в течение часа прибавл ют по капл м 26,4 г диметилацетал ацетоацетальдегида (0,2 г-м.оль. После окончани прибавлени размешивание при той температуре продолжают еш;е 1 час, а затем реакционную смесь в течение 1 час довод т до кипени . Смесь охлаждают до 40° С, прибавл ют при размешивании 50,0 г безводного плавленого хлористого цинка, нагревают до кипени и размешивают при кипении в течение 2,5 час. Спирт отгон ют, остаток при охлаждении обрабатывают 10%-ным водным раствором едкого натра до ш,елочной реакции на лакмус и перегон ют с вод ным паром.To a mixture of 64.0 g of a double tin salt of 2-aminothioften hydrochloride (0.1 g-mol), 250.0 ml of anhydrous ethanol and 5.0 g of anhydrous fused zinc chloride at 65-75 ° C and vigorous stirring for an hour 26.4 g of acetoacetaldehyde dimethyl acetal (0.2 gmol.ol.) is added dropwise. After the addition is complete, stirring at that temperature is continued; e.e for 1 hour, and then the reaction mixture is boiled for 1 hour. to 40 ° C, 50.0 g of anhydrous fused zinc chloride are added with stirring, heated to boiling and stirring ayut at reflux for 2.5 hours. The alcohol was distilled off, the residue was treated under cooling with 10% aqueous sodium hydroxide solution until br, herringbone to litmus and distilled with steam.
Основание перегон етс в виде бесцветных кристаллов. Их отфильтровывают, промывают водой и высушивают над твердой щелочью. Выход 2,9 г (14,li% теоретического). Т. пл. 78-79°С. После кристаллизации из петролейного эфира - бесцветные пластинки с т. пл. 84-85°С.The base is distilled as colorless crystals. They are filtered off, washed with water and dried over solid alkali. Yield 2.9 g (14, li% theoretical). T. pl. 78-79 ° C. After crystallization from petroleum ether - colorless plates with m. Pl. 84-85 ° C.
Пикрат - желтовато-зеленые пластинки (из этанола) ст. пл. 184-185° С.Picrate - yellowish-green plates (of ethanol) Art. square 184-185 ° C.
Пример 2. 2 - м ети л ти е ц о - (3,2 - в) т и е н о - (2,3 -в) -пиридинExample 2. 2 - m aethythi c about - (3,2 - c) t and e n about - (2,3-b) -pyridine
К смеси 55,0 г двойной олов нной соли хлоргидрата 2-аминотиено-(3,2-в) - тиофена (0,085 г-моль), 250 мл безводного этанола и 5,0 г безводного плавленого хлористого цинка при 65-75° С И энергичном размешивании в течение часа прибавл ют по капл м 23,0 г диметилацетал ацетоацетальдегида (0,17 г-моль). Далее синтез ведут аналогично примеру 1. Выход 2,6 г (14,9% теоретического). Т. пл. 81-83° С. После кристаллизации из петролейного эфира - белоснежные пластинки с т. пл. 83-84°С.To a mixture of 55.0 g of a double tin salt of 2-aminothieno- (3,2-b) -thiophene (0.085 g-mol) hydrochloride, 250 ml of anhydrous ethanol and 5.0 g of anhydrous fused zinc chloride at 65-75 ° С 23.0 g of acetoacetaldehyde dimethyl acetal (0.17 g-mol) is added dropwise to vigorous stirring within an hour. Next, the synthesis is carried out analogously to example 1. Output 2.6 g (14.9% of theoretical). T. pl. 81-83 ° C. After crystallization from petroleum ether - white plates with so pl. 83-84 ° C.
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823400608A Addition SU1043785A2 (en) | 1982-03-01 | 1982-03-01 | Device for compensating total current of single-phase earthing |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SU165730A1 SU165730A1 (en) | |
| SU165729A1 SU165729A1 (en) | |
| SU165731A1 true SU165731A1 (en) |
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