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SU1215620A3 - Способ получени метансульфонамида 5-/2-хлор-4-трифторметилфенокси/-2-нитробензойной кислоты - Google Patents

Способ получени метансульфонамида 5-/2-хлор-4-трифторметилфенокси/-2-нитробензойной кислоты Download PDF

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SU1215620A3
SU1215620A3 SU823467843A SU3467843A SU1215620A3 SU 1215620 A3 SU1215620 A3 SU 1215620A3 SU 823467843 A SU823467843 A SU 823467843A SU 3467843 A SU3467843 A SU 3467843A SU 1215620 A3 SU1215620 A3 SU 1215620A3
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USSR - Soviet Union
Prior art keywords
acid
chloro
producing
trifluoromethylphenoxy
methanesulfonamide
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SU823467843A
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English (en)
Inventor
Ибрагим Эйба Эль-Ахмади
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Рон-Пуленк Агрошими (Фирма)
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N1/00—Preservation of bodies of humans or animals, or parts thereof
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
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    • A01N41/04—Sulfonic acids; Derivatives thereof
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
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    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
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    • C07—ORGANIC CHEMISTRY
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    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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    • C07F9/40—Esters thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

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Description

1
Изобретение относитс  к синтезу биологически активных веществ, в частности к способу получени  метан сульфонамида 5-(2-хлор-4-трифтор- метилфенокси)-2-нитробензойной кислоты , про вл ющего гербицидную активность .
Цель изобретени  - повьшение выхода целевого продукта.
Пример 1. Смешивают 2 г (0,01 моль) метансульфамида с 3,8 г (0,01 моль) хлорангидрида 5-2 -хлор -4 -(трифторметилфенокси)-2-нитро- бензойной кислоты. Нагревают смесь в течение 20 мин при 150°С. Из реакционной среды вьщел етс  сол на  кислота по мере образовани . Смесь охлаждают, получают черное масло,которое раствор ют в водном растворе щелочи, фильтруют, подкисл ют фильтрат разбавленной сол ной кислотой, в результате чего выпадает в осадок продукт формулы ().Получают taKHM образом с ВЫХОДОМ 71%, 3,1 г продукта , с Т.пл. 195-197 С и полосой ИК-спектра поглощени  1692 (група ). Продукт имеет следующую формулу
С1C014HSO CH
F3C-(
Пример 2. Работают по методике примера 1, но реакцию осуществл ют при 120 С и провод т ее до окончани  выделени  газообразного НСЕ. Получают сульфонамид с выходом выше 60% с.Т.пл. 195-197°С.
Пример 3. Работают согласно методике примера 1, но осуществл ют реакцию при и провод т ее до окончани  вьщеленн  газообразного НС6. Получают сульфонамид с
Редактор М. Дыпын
Составитель Н. Куликова
Техред Н.Бонкало Корректор А.Обручар
Заказ 2529Тираж 379Подписное
ВНИИПИ Государственен о го комитета СССР
по делам изобретений и открытий 113035, Москва, Ж-35, Раушска  наб., д. 4/5
Производственно-полиграфическое предпри тие, г. Ужгород, ул. Проектна , 4
156202
выходом 2,7 г, вьшш 65%. Т.пл. 195- 197°С.
П р е р 4. Работают согласно методике примера 1, но реакцию осу5 ществл ют при мол рном отношении сульфонамида формулы (III) к хлор- ангидриду кислоты, равном 5. Получают сульфонамид с выходом 2,9 г, вьше 70%, с Т.пл. 195-197°С.
Пример 5. Работают по методике примера 1, но реакцию осуществл ют при мол рном отношении сульфонамида формулы (III) к хлоргнгид- риду кислоты, равном 1,5. Получают
5 сульфонамид с выходом 2,5 г, вьппе 55%, с Т.гш. 195-197 с.
Пример 6 (прототип). 1,58 г ацифторфена (2-хлор-4-трифторметил- фенокси)-2-нитробензойной кислоты
20 нагревают с обратным охлаждением с 20 мл SOCEJ в течение 90 мин. Избыток дистиллируют в вакууме, в масл нистый осадок выбирают 20 мп пиридина. Добавл ют 0,45 г метан25 сульфонамида и перемешивают одну ночь при комнатной температуре. Пиридин дистиллируют в вакууме, а оставшеес  масло смешивают с хлористоводородной кислотой 2 N и затем эк30 страгируют эфиром (2 раза по 100 мл). Эфирные экстракты промывают 100 мл воды, высушивают и выпаривают в вакууме. Твердый осадок перекрис- таллизовывают в изопропаноле дл 
35 получени  метансульфонамида производного от ацифторфена с мол рным вы:х;одом 41%, т.е. получают 0,76 г продукта.
Предложенный способ позвол ет по40 лучить целевой продукт с выходом 55- 71% (41% в известном способе), а также упростить процесс за счет исключени  акцептора хлористого водорода .

Claims (1)

  1. СПОСОБ ПОЛУЧЕНИЯ МЕТАНСУЛЬФОНАМИДА 5-(2-ХЛОР-4-ТРИФТОРМЕТИЛФЕН0КСИ)-2-НИТР0БЕН30ЙН0Й КИСЛОТЫ формулы
    Ct C0NHS0aCH3
    ГзС-^0/-о-@>-ыог путем взаимодействия хлорангидрида кислоты формулы
    С1 СОС1 с сульфамидом формулы
    СН3 SO2 NH2 , III отличающийся тем, что, с целью повышения выхода целевого продукта, процесс осуществляют при молярном соотношении сульфамида к хлорангидриду, равном (1-5):1 и температуре 120-160 С.
SU823467843A 1981-07-27 1982-07-26 Способ получени метансульфонамида 5-/2-хлор-4-трифторметилфенокси/-2-нитробензойной кислоты SU1215620A3 (ru)

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EP0003416B1 (en) * 1978-01-19 1981-08-26 Imperial Chemical Industries Plc Diphenyl ether compounds useful as herbicides; methods of using them, processes for preparing them, and herbicidal compositions containing them
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Европейский патент № 0023392, кл. С 07 С 143/72, 1980. Европейский патент ff 0003416, кл. С 07 С 143/72, 1979. *

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JPS5826860A (ja) 1983-02-17
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IL66197A (en) 1985-11-29
KR880002591B1 (ko) 1988-12-03
BR8204357A (pt) 1983-07-19
RO85388A (ro) 1984-11-25
PT75322A (fr) 1982-08-01
LU84295A1 (fr) 1984-03-22
DK333282A (da) 1983-01-28
AT385985B (de) 1988-06-10
IE53978B1 (en) 1989-05-10
ES8306108A1 (es) 1983-05-01
PL136683B1 (en) 1986-03-31
FR2510105A1 (fr) 1983-01-28
BE893940A (fr) 1983-01-26
PT75322B (fr) 1985-11-29
IT8222545A0 (it) 1982-07-23
ATA290082A (de) 1987-11-15
IT8222545A1 (it) 1984-01-23
IT1198399B (it) 1988-12-21
FR2510105B1 (ru) 1984-09-07
GB2103611A (en) 1983-02-23
GB2103611B (en) 1985-04-03
IE821786L (en) 1983-01-27
IL66197A0 (en) 1982-11-30
DD203716A5 (de) 1983-11-02
HU191186B (en) 1987-01-28
JPH0149262B2 (ru) 1989-10-24
PL237639A1 (en) 1983-05-23
KR840000466A (ko) 1984-02-22
DE3227847A1 (de) 1983-02-10
CA1194472A (en) 1985-10-01
ES514352A0 (es) 1983-05-01

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