SU213815A1 - Method of producing amides and anilides of carboxylic acids - Google Patents
Method of producing amides and anilides of carboxylic acidsInfo
- Publication number
- SU213815A1 SU213815A1 SU899552A SU899552A SU213815A1 SU 213815 A1 SU213815 A1 SU 213815A1 SU 899552 A SU899552 A SU 899552A SU 899552 A SU899552 A SU 899552A SU 213815 A1 SU213815 A1 SU 213815A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carboxylic acids
- anilides
- producing amides
- acid
- amides
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title description 6
- 150000001735 carboxylic acids Chemical class 0.000 title description 2
- 229940051881 Anilide analgesics and antipyretics Drugs 0.000 title 1
- 150000003931 anilides Chemical class 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000005631 2,4-D Substances 0.000 description 1
- VGVRFARTWVJNQC-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(Cl)C=C1Cl VGVRFARTWVJNQC-UHFFFAOYSA-N 0.000 description 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
- WZXVNTKQBLHNJC-UHFFFAOYSA-N CC[N-]CC.OC(=O)COC1=CC=CC=C1 Chemical compound CC[N-]CC.OC(=O)COC1=CC=CC=C1 WZXVNTKQBLHNJC-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- GQZXNSPRSGFJLY-UHFFFAOYSA-N Hypophosphorous acid Chemical compound OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 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
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
Изобретение относитс к области получени производных карбоновых кислот, в частности, амидов , Примен ющихс в сельском хоз йстве и медицинской практике.The invention relates to the field of the production of carboxylic acid derivatives, in particular, amides, used in agriculture and medical practice.
Предложен способ получени амидов и аш1лидов карбановых кислот, который состоит в том, что «арбоновую кислоту подвергают взаимодействию с аммиаком, амииами, или анилином в присутствии фо сфористой или фосфинистой кислоты (или их производных) в качестве катализатора п.ри нагревании в среде органического растворител с азеотропной отгонкой 1воды. Выход достигает 80-90о/о.A method has been proposed for producing amides and Ash1lides of carboxylic acids, which consists in the fact that "arbonic acid is reacted with ammonia, ammonia, or aniline in the presence of phosphoric or phosphinic acid (or their derivatives) as a catalyst after heating in organic solvent. with azeotropic distillation of water. The output reaches 80-90o / o.
Пример 1. Амид 2,4-ДИ X л о р ф е,н о ксиу ксусной кислоты (2,4-Д). В стекл иную трубку, снабженную насадкой Дина- Старка и барботеро,.м, помещают 11,05 г 2,4-Д, 0,2 г треххлористого фосфора, 30 л технического трихлорбензола (т. КИ1П. 205- 215° С) и 10 мл ксилола (ловушку насадки заполн ют ксилолом). Реакционную смесь нагревают до кипени и в полученный гомогенный раствор барботируют аммиак со скоростью 5-10 г/час (высота барботажного сло 10 Cvii). Конец реакции определ ют по прекр1ащен1ию выделени воды (через 1,5- 2 час воды выдел етс теоретическое количество ). При охлаждении реакционной массы обр азовавшийс амид выпадает в виде кристаллов и его отдел ют фильтров-анием. Выход lOOVo; т. пл. 154-155° С (из метанола). Литературные данные: т. пл. 155-156° С.Example 1. Amide 2,4-DI X l o r f e, n o xiu xusic acid (2,4-D). 11.05 g of 2.4-D, 0.2 g of phosphorus trichloride, 30 l of technical trichlorobenzene (m. KI1P. 205-215 ° C) and 10 ml of xylene (the nozzle trap is filled with xylene). The reaction mixture is heated to boiling and ammonia is bubbled into the resulting homogeneous solution at a rate of 5–10 g / h (height of the 10 Cvii bubble layer). The end of the reaction is determined by the pre elimination of water release (after 1.5-2 hours, the theoretical amount is released). When the reaction mass is cooled, the formed amide precipitates as crystals and is separated by filtration. Output lOOVo; m.p. 154-155 ° C (from methanol). Literary data: so pl. 155-156 ° C.
Аиалогично протекает реакци при использовании Б качестве катализатора фосфористой кислоты (2 мол. %).Similarly, the reaction proceeds using B as a catalyst for phosphorous acid (2 mol.%).
Пример 2. Амид ф е оксиу к су сн о и кислоты. Получен в услови х синтеза амида 2,4-Д. Выход т. пл. 99-100° С (из спирта). Литературные данные: т. пл. 101,5° С.Example 2. Amide f e oxy cus cn o and acid. Obtained under the conditions of synthesis of 2,4-D amide. Exit t. PL. 99-100 ° C (from alcohol). Literary data: so pl. 101.5 ° C.
Пример 3. Диэтиламид феноксиуксусной кислоты. В круглодонную колбу с «асадкой Дина-Старка помещают 0,05 г моль феноксиуксусной кислоты, 0,06 г моль диэтиламииа, 0,001 г-моль фосфористой кислоты, 20 мл трихлорбензола и 30 мл ксилола. Реакционную .смесь перемешивают 5-10 мин, затем кип т т до ирекращени отгонки воды (2-3 час). После охлаждеии смесь разбавл ют 50 мл эфира (или бензола ), про.мывают водой, сушат над сульфатом магни (или азеотропно) и продукт выдел ют .перегонкой. Выход 80%, т. кии. 142-Example 3. Diethylamide phenoxyacetic acid. In a round bottom flask with a Dean-Stark precipitate, 0.05 g mol of phenoxyacetic acid, 0.06 g mol of diethylamine, 0.001 g mol of phosphorous acid, 20 ml of trichlorobenzene and 30 ml of xylene are placed. The reaction mixture is stirred for 5-10 minutes, then boiled until the water is distilled off (2-3 hours). After cooling, the mixture is diluted with 50 ml of ether (or benzene), washed with water, dried over magnesium sulfate (or azeotropic) and the product is isolated by distillation. Output 80%, because the cues. 142-
плолfoul
143° с (2 мм рт. ст.}- df 1,0760; По 1,5290; MRo 59,28, вычислено 59-35. Литературные данные: т. кип. 152-154° С (6 мм рт. ст.).143 ° C (2 mm of mercury.} - df 1.0760; 1.5290; MRo 59.28, calculated 59-35. Literary data: boils. 152-154 ° С (6 mm of mercury .).
Таблица 1Table 1
Таблица 2table 2
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU213815A1 true SU213815A1 (en) |
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