SU617010A3 - Способ получени бис-(2-метил-3окси-5-винилпиридил-4-метил)дисульфида или его солей - Google Patents

Способ получени бис-(2-метил-3окси-5-винилпиридил-4-метил)дисульфида или его солей

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Publication number
SU617010A3
SU617010A3 SU742036119A SU2036119A SU617010A3 SU 617010 A3 SU617010 A3 SU 617010A3 SU 742036119 A SU742036119 A SU 742036119A SU 2036119 A SU2036119 A SU 2036119A SU 617010 A3 SU617010 A3 SU 617010A3
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USSR - Soviet Union
Prior art keywords
methyl
solution
disulfide
hydroxy
salts
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SU742036119A
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English (en)
Inventor
Джонс Говард (Великобритания)
Винг Кин Ли Томас (Гон-Конг)
Шен Цунг-Йинг (Сша)
Питер Дорн Конрад (Сша)
Густав Хазен Джордж (Сша)
Грегори Мелилло Дэвид (Сша)
Слетзингер Мейер (Сша)
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Мерк Энд Ко Инк (Фирма)
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/48—Aldehydo radicals
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D263/36—One oxygen atom
    • C07D263/42—One oxygen atom attached in position 5
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
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    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings

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  • Pyridine Compounds (AREA)

Description

ной кислотой, надуксусной кислотой, надфталевсй кислотой, гипохлоритом натри , йодом или перекисью водорода, в водном растворе при О-15°С.
Пример 1. Хлоргидрат 2-метил-3-окси-4-.меркапто .метнл-5-винил пиридина.
A.Получение 3,4-а-ди-О-изопропилиденпроизводного 2-метил-3-окси-4-оксиметил-5-винилпиридина .
67 мл н-бутиллити  (1,9 М раствор в н-гексане ) подают в перемешиваемую суспензию 42,7 г (0,12 моль) бромистого трифенилметилфосфони  при комнатной температуре в среде 300 J тетрагидрофурапа в атмосфере азота. К этому перемешиваемому раствору добавл ют раствор 24,7 г (0,119 моль) 3,4-а-ди-О-изопропилиденпроизводного 2-метил-3-окси-4-оксиметил-5-формилпиридина в 300 мл тетрагидрофурана по капл м в течение 1 час. Реакцию продолжают в течение 1 час при комнатной температуре, а затем реакционную смесь кип т т с обратны.м холодильником в течение 4 час.
Раствор упаривают досуха сначала под ва .куумом, а затем подсушивают в глубоком вакуу .ме при 30-50°С. Остаток в виде красного масла растирают с 400 мл эфира. Твердую окись трифенилфосфина отфильтровывают (17,0 г), а- эфирный фильтрат экстрагируют дважды (по 200 мл) насыщенны. растворо.м бисульфита натри  и упаривают досуха, образуетс  .масло красновато-желтого цвета. Продукт примен ют на следующей стадии без дополнительной очистки.
Б. Получение хлоргидрата 2-метил-З-окси-4-оксиметил-5-винил пиридина.
Раствор красного масла, полученный в примере 1А (25 г, 0,122 моль), перемешивают в 500 мл 2,5 н.сол ной кислоты и 500 мл ацетона при кип чении в атмосфере азота в течение 1,5 час. Ацетон отгон ют до температуры 90°С и охлажденный раствор экстрагируют этилацетатом (3 X 400 мл). Водный слой выливают в 700 мл насыщенного раствора бикарбоната натри .
Водный слой экстрагируют этил ацетатом (1 X 400 мл). Органический раствор высушивают сульфатом магни , фильтруют и упаривают с получением беловатого твердого вещества, которые перекристаллизовывают из этилацетата . Получают 9,4 г продукта, т.пл. 164-16б°С.
B.Получение хлоргидрата 2-метил-З-окси-4-меркапто .метил-5-винил пиридина.
В литровую трехгорлую колбу, .снабженную трубкой дл  подвода азота, термометром и воронкой , расположенной в верхней части холодильника , ввод т 530 мл этанола и 53,4 г едкого натра. После образовани  раствора добавл ют 50 г продукта из примера 1Б. К полученному раствору в атмосфере азота прикапывают 30 мл сероуглерода в течение 30 .мин. при перемешивании и 10-15 С. Полученную смесь перемешивают в течение 30 мин, после чего ее охлаждают до 15°С, добавл ют по капл м еще
20 мл сероуглерода и кип т т с.месь с обратным холодильником в течение 4 час.
Реакционную смесь охлаждают до 10°С и добавл ют концентрированный раствор со,1Яной кислоты до рН 2 (80 мл). Смесь выдерживают -на лед ной бане в течение ночи и концентрируют при пониженном давлении (температура бани 20°С) дл  удалени  этанола.
Полученную реакционную смесь (в атмосфере азота) добавл ют к холодной перемешиваемой суспензии 120 г бикарбоната натри  в 1 л воды.
Органический слой экстрагируют трижды (по 300 мл) этилацетатом в отсутствие воздуха. Соединенные экстракты высушивают сульфатом магни , фильтруют и концентрируют при пониженном давлении. Остаток подвергают хроматографической очистке на 1 кг силикагел , эл юент- этила цетат.
Подход щие фракции, что определ етс  в
результате тонкослойной хроматографии с применение .м этилацетата, соедин ют и конце1ггрируют до подход щего объема с получением
свободного основани  в виде белых кристаллов.
Перва  фракци : 33 г, т.пл. 115-117°С.
Втора  фракци : 6 г, т.пл. 114-116°С.
Найдено, «/о: С 59,64; Н 6,35; N 7,26; S 17,3.
CgHllNOS
Вычислено,/,,: С 59,66: Н 6,12; 7.73 S 17,7.
Полученное соединение превращают в хлоргидрат по следующей методике.
Свободное основание (39 г) раствор ют в 500 .мл сухого тетрагидрофурана и при пере .мешивании ввод т сухой хлористый водород, поддержива  температуру ниже 25°С.
Полученный белый осадок отфильтровывают , промывают тетрагидрофураном и высушиBatoT под вакуумо.м. Получают 45 г продукта, т.пл. 149-152°С.
Найдено, /о: С 49,87; Н 5,82; N 6,44; S 15,10.
CiH: .NOSCl
Вычислено, %: С 49,65: Н 5,56: N 6,44;
S 14,73.
Пример 2. Быс-(2-метил-3-окси-5-винил-4-пиридилметил )дисульфид.
9 г хлоргидрата 2-метил-3-окси-4-меркаптометил-5-винилпиридина раствор ют в 50 мл воды и к этому раствору добавл ют 2н. раствор гидроокиси ам.мони  до рН 9. Через раствор в течение 24 час барботируют воздух. Выпавший осадок бис- (2-.метил-3-окси-5-вини;1-4-пиридилметил )дисульфида отфильтровывают и высущивают , т.пл. 178-180°С (с разложением), выход 64/о.
Пример 3. «с-(2-метил-3-окси-5-винил-4-пиридил .метил)дисульфид.
4,36 г хлоргидрат 2-метил-3-окси-4-меркаптометил-5-винилпиридина раствор ют в 40 мл воды при 2-7°С в атмосфере азота. К этому раствору добавл ют 2,0 мл ЗО /о-ного раствора iio ieKiicn водорода в течение д01)/кан11И температуры Поеле перемешивайи  в течение 30 мин при этой температуре емесь фильтруют и в атмосфере азота фильтрат смешивают с избытком насыщенного раствора бикарбоната натри  при 2С в течение 10 мин. Смесь быстро отфильтровывают и осадок на фильтре промывают дважды (по 40 мл) ацетонитрилом. Твердый продукт и:..ивают над фосфорным ангидридом и по |учают 1.5 г б«с-(2-метил-3-окси-5-ви НИЛ-4-пиридил метил) дисульфида т. пл. выше 300°С, т. пл. моногидрата составл ет 178-180°С. при 1одФормула изобр111 ни  ( люсоб пол чени  бис- |2-мети.-1-3-окси-5-вин )1.;п1ириди.1-4-метил)дисхльфида и.ти его солей , отличающийс  те.м, что 2-метил-3-окси-4- .меркаптометил-5-вииилпирид11н подвергают взаимодействию с кислородом воздуха или перекисью водорода и целевой продукт выдел ют в виде основани  и.пи соли. Источники информации, прин тые во внимание при экспертизе: 1. Вейганд-Хилгетат. Методы эксперимента в органической химии, М.. «Хими , 1968, с. 609. Приоритеты ПС признакам: 15.06.73при примеиеиии кислорода воздуха; 26.04.74при применении перекиси водорода.
SU742036119A 1973-06-15 1974-06-14 Способ получени бис-(2-метил-3окси-5-винилпиридил-4-метил)дисульфида или его солей SU617010A3 (ru)

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US36877273A 1973-06-15 1973-06-15
US46401174A 1974-04-26 1974-04-26

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SU617010A3 true SU617010A3 (ru) 1978-07-25

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AT (1) AT346845B (ru)
DD (1) DD115665A5 (ru)
HU (1) HU170468B (ru)
OA (1) OA04933A (ru)
PL (1) PL90632B1 (ru)
SU (1) SU617010A3 (ru)

Also Published As

Publication number Publication date
PL90632B1 (ru) 1977-01-31
HU170468B (ru) 1977-06-28
AT346845B (de) 1978-11-27
ATA481174A (de) 1978-04-15
DD115665A5 (ru) 1975-10-12
OA04933A (fr) 1980-10-31

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