SU426362A3 - METHOD FOR OBTAINING DICHLORBENZYLTHYOETHYLAMINES - Google Patents
METHOD FOR OBTAINING DICHLORBENZYLTHYOETHYLAMINESInfo
- Publication number
- SU426362A3 SU426362A3 SU1337524A SU1337524A SU426362A3 SU 426362 A3 SU426362 A3 SU 426362A3 SU 1337524 A SU1337524 A SU 1337524A SU 1337524 A SU1337524 A SU 1337524A SU 426362 A3 SU426362 A3 SU 426362A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- obtaining
- general formula
- dichlorobenzylthio
- ethylamine
- dichlorbenzylthyoethylamines
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
Description
Изобретение относитс к области получени новых замещенных бензилмеркаптанов, а именно дихлорбензилтиоэтиламинов общей формулы I -СН.гЗСНгСН :КНг С1I или их солей, обладающих ценными пестицидными свойствами. Предлагаемые соединени вл ютс новыми и могут найти применение в сельском хоз йстве в качестве биологически активных веществ, а также в бумажной промышленности . Известен способ получени р-бензиламиноэтилмеркаптана взаимодействием этиленсульфида с р-бепзиламином в среде абсолютного бензола. Однако способ получени соединений общей формулы I, обладающих ценными пестицидными свойствами, в литературе не описан. Согласно данному изобретению описываетс способ получени неописанных в литературе дихлорбензилтиоэтиламинов общей формулы I, или их солей, заключающийс в том, что дихлорбеизилмеркаитан общей формулы II CH.SH С1 и подвергают взаимодействию с этилеиимином, с последующим выделением целевого продукта в виде основани или соли. Конденсацию дихлорбензилмеркаптана с этнленимином предпочтительно провод т в среде органического растворител , например, этилового или метилового спирта, тетрагидрофурапа или четыреххлористого углерода. В зависимости от условий способа целевые продукты получают в свободной форме или в виде соли. Соединени общей формулы I могут быть переведены в соль обычным способом , например при помощи обработкп органического растворител или в смеси воды и одного или нескольких органических растворителей . Пример 1. Получение р-(3,4-дихлорбензилтио ) -этиламина (А). В охлажденную до 0°С смесь 30 г 3,4-дихлорбепзилмеркаптана и 133 см абсолютного этанола, ввод т, в течение около 15 мин, 9 г бидистилл та этиленимина. Затем температуру реакционной среды довод т до 20° С и перемешивают в течепие 3 час. Спирт перегон ют при пониженном давлении, ректифидиругот остаток и получают таким образом 29,9 г р-(ЗД-дихлорбензилтио)-этиламина; т. кип.: 128° С (0,1 мм. рт. ст.); По 1,597. Мол. вес. 236,2.The invention relates to the field of the preparation of new substituted benzyl mercaptans, namely, dichlorobenzylthioethylamines of the general formula I -C.H3CHNgSN: KNg C1I or their salts with valuable pesticidal properties. The proposed compounds are new and can be used in agriculture as biologically active substances, as well as in the paper industry. A known method for producing p-benzylaminoethyl mercaptan by reacting ethylene sulfide with p-bepsylamine in absolute benzene. However, the method of obtaining compounds of general formula I possessing valuable pesticidal properties is not described in the literature. According to the present invention, a method for the preparation of dichlorobenzylthioethylamines of general formula I or their salts not described in the literature is described. The condensation of dichlorobenzylmercaptan with ethnlenimine is preferably carried out in an organic solvent medium, for example ethyl or methyl alcohol, tetrahydrofurap or carbon tetrachloride. Depending on the conditions of the method, the target products are obtained in free form or in the form of a salt. Compounds of general formula I can be salified in a conventional manner, for example, by treating an organic solvent or in a mixture of water and one or more organic solvents. Example 1. Obtaining p- (3,4-dichlorobenzylthio) -ethylamine (A). Into a mixture of 30 g of 3,4-dichloro-benzyl mercaptan and 133 cm of absolute ethanol cooled to 0 ° C, for about 15 minutes, 9 g of bidistille ethyleneimine is added. Then the temperature of the reaction medium is brought to 20 ° C and stirred for 3 hours. The alcohol is distilled under reduced pressure, and the residue is rectified and thus 29.9 g of p- (3H-dichlorobenzylthio) -ethylamine are obtained; ton boil: 128 ° С (0.1 mm. Mercury); 1,597 each. Mol weight. 236.2.
Вычислено, %: С 45,8; Н 4,68; С1 30,04; N5, 92; S 13,56.Calculated,%: C 45.8; H 4.68; C1 30.04; N5, 92; S 13.56.
CgHnCbNS.CgHnCbNS.
Найдено, %: С 46,1; Н 4,80; С1 30; N 5,6; S 13,4.Found,%: With 46.1; H 4.80; C1 30; N 5.6; S 13.4.
Хлоргидрат соединени А - твердый продукт; т. ил. 175° С.Compound A hydrochloride is a solid product; T. Il. 175 ° C
Пример 2. Получение р-(2,4-дихлорбеизилтио )-этиламина (В).Example 2. Obtaining p- (2,4-dichloroisylthio) -ethylamine (B).
Работа таким же способом, как и в примере 1, и исиользу 30 г 2,4-дихлорбепзилмеркаптана , растворенного в 133 см абсолютного этанола, и 9 г бидистилл та этиленимина , получают 30,22 г р-(2,4-дихлорбензилтио)этиламииа; т. кии. 118-120°С (0,1 ммрт.ст.); Working in the same manner as in Example 1, and using 30 g of 2,4-dichlorbopzil-mercaptan dissolved in 133 cm of absolute ethanol and 9 g of bidistillate ethyleneimine, 30.22 g of p- (2,4-dichlorobenzylthio) ethylamine ; t. cues. 118-120 ° C (0.1 mmHg);
По 1,5965. Мол. вес. 236,2.1.5965 each. Mol weight. 236.2.
Вычислено, %: С-45,8; Н 4,68; С1 30,04; N 5,92; S 13,56.Calculated,%: C-45.8; H 4.68; C1 30.04; N 5.92; S 13.56.
CgHisCbNS.CgHisCbNS.
Найдено, %: С 45,6; Н 4,7; С1 30,2; N 5,6; S 13,4.Found,%: С 45.6; H 4.7; C1 30.2; N 5.6; S 13.4.
Хлоргидрат соединени В - твердый продукт; т. пл. 140° С.Compound B hydrochloride is a solid product; m.p. 140 ° C
Аналогичным способом иолучены:In a similar way and obtained:
р- (2,3-дихлорбензилтио) -этиламии; |3- (2,5-дихлорбензилтио) -этиламин; Р- (2,6-дихлорбензилтио) -этиламин; Р- (3,5-дихлорбензилтио) -этиламин.p- (2,3-dichlorobenzylthio) ethylamino; 3- (2,5-dichlorobenzylthio) -ethylamine; P- (2,6-dichlorobenzylthio) -ethylamine; P- (3,5-dichlorobenzylthio) -ethylamine.
Предмет изобретени Subject invention
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR154123 | 1968-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU426362A3 true SU426362A3 (en) | 1974-04-30 |
Family
ID=8650904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1337524A SU426362A3 (en) | 1968-06-07 | 1969-06-06 | METHOD FOR OBTAINING DICHLORBENZYLTHYOETHYLAMINES |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4937245B1 (en) |
| BE (1) | BE734108A (en) |
| DE (1) | DE1928857A1 (en) |
| FR (1) | FR1584548A (en) |
| GB (1) | GB1224676A (en) |
| NL (1) | NL6908418A (en) |
| NO (1) | NO130263B (en) |
| SE (1) | SE358159B (en) |
| SU (1) | SU426362A3 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3316009A1 (en) * | 1983-05-03 | 1984-11-08 | LINHOF Präzisions-Kamera-Werke GmbH, 8000 München | Rotary focal plane shutter for photographic cameras |
| US5298483A (en) * | 1992-03-30 | 1994-03-29 | Tropicana Products, Inc. | New matter of composition and method for using the same as plant bioregulators |
| US5324707A (en) * | 1992-03-30 | 1994-06-28 | Tropicana Products, Inc. | Method of in vitro application of bioregulator compounds |
| DE19609414C1 (en) * | 1996-03-04 | 1997-07-31 | Arnold & Richter Kg | Motion picture camera |
-
1968
- 1968-06-07 FR FR1584548D patent/FR1584548A/fr not_active Expired
-
1969
- 1969-05-21 SE SE721769A patent/SE358159B/xx unknown
- 1969-05-29 JP JP4143969A patent/JPS4937245B1/ja active Pending
- 1969-06-03 NL NL6908418A patent/NL6908418A/xx unknown
- 1969-06-05 BE BE734108D patent/BE734108A/xx unknown
- 1969-06-05 GB GB2838869A patent/GB1224676A/en not_active Expired
- 1969-06-06 NO NO235369A patent/NO130263B/no unknown
- 1969-06-06 SU SU1337524A patent/SU426362A3/en active
- 1969-06-06 DE DE19691928857 patent/DE1928857A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE734108A (en) | 1969-12-05 |
| FR1584548A (en) | 1969-12-26 |
| JPS4937245B1 (en) | 1974-10-07 |
| DE1928857A1 (en) | 1970-01-22 |
| SE358159B (en) | 1973-07-23 |
| GB1224676A (en) | 1971-03-10 |
| NO130263B (en) | 1974-08-05 |
| NL6908418A (en) | 1969-12-09 |
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