SU520048A3 - The method of obtaining 3pyrrolidinyl-1-propyldithiocarbamic acid - Google Patents

The method of obtaining 3pyrrolidinyl-1-propyldithiocarbamic acid

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Publication number
SU520048A3
SU520048A3 SU2116859A SU2116859A SU520048A3 SU 520048 A3 SU520048 A3 SU 520048A3 SU 2116859 A SU2116859 A SU 2116859A SU 2116859 A SU2116859 A SU 2116859A SU 520048 A3 SU520048 A3 SU 520048A3
Authority
SU
USSR - Soviet Union
Prior art keywords
temperature
acid
obtaining
propyldithiocarbamic
carried out
Prior art date
Application number
SU2116859A
Other languages
Russian (ru)
Inventor
Зассе Клаус
Фробергер Пауль-Эрнст
Original Assignee
Баейр Аг., (Фирма)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Баейр Аг., (Фирма) filed Critical Баейр Аг., (Фирма)
Application granted granted Critical
Publication of SU520048A3 publication Critical patent/SU520048A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Изобретение относитс  к способу получени  ол идинил- l-np опилдити окарб ами- новой кислоты, котора  находит применение в качестве фунгицида. Известен способ получени  3-пирролидинш1-1-пропилдитиокарбаминовой кислоты путем взаимодействи  1-(3-аминопропил)-пирролидина с сероуглеродом при 25 С в среде бензола ij. Целевой продукт выдел ют известными приемами, например фильтрацией, т.пл. 147-149°С . Недостаток известного способа состоит в том, что целевой продукт нельз  получить с достаточной степенью чистоты, Дл  повышени  чистоты целевого продук та предложено процесс получени  3-пирропидинил-1- дитиокарбаминовой кислоты формулы i -CHiCHiCHj-UH-(t-sH ,-MI-LsH() вести в одной среде при температуре от -10 до + 50 С, предпочтительно при температуре 0-30 С. Целевой продукт выдел ют Б свободном виде или в виде внутренней соли. Данный способ позвол ет получить 3-пир- ропидинил-1-пропилдитиокарбаминовую кислоту с т.пл, 175 С. Выход конечного продукта составл ет 95% от теории, Данное изобретение иллюстрируетс  нижеприведенным примером. Пример 1, В раствор из 128 г (1 моль) 1-(3-аминопропил)-пирролидина в 600 мл воды прибавл ют при температуре 10-15 С, 76 г (1 моль) сероуглеводорода. Затем смесь размешивают в течение 1 час при комнатной температуре, кристаллизат отсасывают, промывают лед ной водой, метанолом и высушивают. Получают 194 г З-пирролидинил-1-пропилдитиокарбаминовой кислоты; с т.пл, 175 С; выход 95% от теории . Полученное соединение может быть повторно перекристаллизовано из воды, 175 С ( при разложении).The invention relates to a process for the preparation of an ol idinyl-l-np opildite okarb amic acid, which finds use as a fungicide. A known method for producing 3-pyrrolidinsh1-1-propyldithiocarbamic acid by reacting 1- (3-aminopropyl) -pyrrolidine with carbon disulfide at 25 ° C in benzene ij. The desired product is isolated by known techniques, for example filtration, m.p. 147-149 ° C. A disadvantage of the known method is that the target product cannot be obtained with a sufficient degree of purity. To increase the purity of the target product, a process has been proposed for the preparation of 3-pyrrolidinyl-1-dithiocarbamic acid of formula i -CHiCHiCHj-UH- (t-sH, -MI-LsH () Conduct in one medium at a temperature of from -10 to + 50 ° C, preferably at a temperature of 0-30 ° C. The desired product is isolated in free form or as an internal salt. This method allows to obtain 3-pyrropidinyl-1- propyldithiocarbamic acid with m.p., 175 C. The yield of the final product is 95% of theory. The invention is illustrated by the following example. Example 1, To a solution of 128 g (1 mol) of 1- (3-aminopropyl) -pyrrolidine in 600 ml of water was added at a temperature of 10-15 C, 76 g (1 mol a) hydrocarbon. Then the mixture is stirred for 1 hour at room temperature, the crystallized precipitate is filtered off with suction, washed with ice water, methanol and dried to give 194 g of 3-pyrrolidinyl-1-propyldithiocarbamic acid; with mp, 175 ° C; yield 95% of theory. The compound obtained can be recrystallized from water, 175 C (during decomposition).

33

Вычислено, %: N 13,7; 5 31,35.Calculated,%: N 13,7; 5 31.35.

Найдено, %: ЛЗ,8; S 31,30.Found,%: LZ, 8; S 31.30.

Claims (1)

Формула изобретени Invention Formula 1, Способ получени  З-пирролидинил-1-пропилдитиокарбаминовой кислоты формулы1, Method for preparing 3-pyrrolidinyl-1-propyl dithiocarbamic acid of formula ОABOUT H-CHiCHjCHj-lffl - с - SHH-CHiCHjCHj-lffl - s - SH илиor 77 GG Н-СНг(Я,(Нг-МК-3-8н(-)N-SNg (I, (Ng-MK-3-8n (-) путем взаимодействи  1-(3-аминопропил)-by reacting 1- (3-aminopropyl) - 520048520048 -пирролидина с сероуглеродом в среде растворител , отличающийс  тем, что, с целью повышени  степени чистоты целевого продукта, в качестве растворител  примен ют воду, и процесс ведут при температуре от -10 до +50°С,-pyrrolidine with carbon disulfide in a solvent medium, characterized in that, in order to increase the purity of the target product, water is used as the solvent, and the process is carried out at a temperature from -10 to + 50 ° C, 2 Способ по п, 1, отличающийс  TSMj что процесс ведут при температуре 0-30 С.2 The method according to claim 1, wherein the process is carried out at a temperature of 0-30 C. Источники информации, прин тые во вн мание при экспертизе:Sources of information taken into account in the examination: 151. Патент США № 2.971.884, кл. 424-267 , опубл. 14.02.61,151. US Patent No. 2.971,884, cl. 424-267, publ. 14.02.61,
SU2116859A 1974-04-09 1975-03-26 The method of obtaining 3pyrrolidinyl-1-propyldithiocarbamic acid SU520048A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2417142A DE2417142A1 (en) 1974-04-09 1974-04-09 PROCESS FOR PREPARING 3-PYRROLIDINYL- (1) -PROPYL-DITHIOCARBAMIC ACID

Publications (1)

Publication Number Publication Date
SU520048A3 true SU520048A3 (en) 1976-06-30

Family

ID=5912516

Family Applications (1)

Application Number Title Priority Date Filing Date
SU2116859A SU520048A3 (en) 1974-04-09 1975-03-26 The method of obtaining 3pyrrolidinyl-1-propyldithiocarbamic acid

Country Status (17)

Country Link
BE (1) BE827187A (en)
CH (1) CH597211A5 (en)
CS (1) CS177043B2 (en)
DD (1) DD119590A5 (en)
DE (1) DE2417142A1 (en)
DK (1) DK136472C (en)
FR (1) FR2267320B1 (en)
GB (1) GB1455683A (en)
HU (1) HU172754B (en)
IE (1) IE40891B1 (en)
IL (1) IL47009A (en)
IT (1) IT1049401B (en)
LU (1) LU72226A1 (en)
NL (1) NL7504119A (en)
PL (1) PL93129B1 (en)
RO (1) RO65068A (en)
SU (1) SU520048A3 (en)

Also Published As

Publication number Publication date
BE827187A (en) 1975-09-26
DK134075A (en) 1975-10-10
GB1455683A (en) 1976-11-17
HU172754B (en) 1978-12-28
LU72226A1 (en) 1976-03-02
IL47009A0 (en) 1975-06-25
IL47009A (en) 1977-11-30
NL7504119A (en) 1975-10-13
IE40891L (en) 1975-10-09
IT1049401B (en) 1981-01-20
RO65068A (en) 1979-02-15
CH597211A5 (en) 1978-03-31
DK136472C (en) 1978-03-28
PL93129B1 (en) 1977-05-30
CS177043B2 (en) 1977-07-29
FR2267320A1 (en) 1975-11-07
DE2417142A1 (en) 1975-10-30
FR2267320B1 (en) 1978-09-29
DK136472B (en) 1977-10-17
IE40891B1 (en) 1979-09-12
DD119590A5 (en) 1976-05-05

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