SU923370A3 - Process for producing 3,4-dimethoxy-6-(4-(2-furoyl)-1-piperazinylthiocarbamido) benzonitrile - Google Patents

Process for producing 3,4-dimethoxy-6-(4-(2-furoyl)-1-piperazinylthiocarbamido) benzonitrile Download PDF

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SU923370A3
SU923370A3 SU772555751A SU2555751A SU923370A3 SU 923370 A3 SU923370 A3 SU 923370A3 SU 772555751 A SU772555751 A SU 772555751A SU 2555751 A SU2555751 A SU 2555751A SU 923370 A3 SU923370 A3 SU 923370A3
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dimethoxy
furoyl
piperazinylthiocarbamido
benzonitrile
formula
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SU772555751A
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Russian (ru)
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Юхани Хонканен Эркки
Кулликки Пиппури Айно
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Орион Ихтюмя Ой (Инофирма)
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

3,4-Dimethoxy-6-[4-(2-furoyl)-1-piperazinylthiocarbamido]-benzonitr ile of the formula II is prepared by reacting 3,4-dimethoxy-6-isothiocyanatobenzonitrile with thiophosgene to give 3,4-dimethoxy-6-isothiocyanatobenzonitrile and reacting the compound which has been obtained with 1-(2-furoyl)piperazine. Alternatively, 1-(2-furoyl)piperazine can be reacted with thiophosgene to give 4-(2-furoyl)piperazinylthiocarbonyl chloride and the compound which has been obtained can be reacted with 3,4-dimethoxy-6-aminobenzonitrile. 3,4-Dimethoxy-6-[4-(2-furoyl)-1-piperazinylthiocarbamido]benzo-nitr ile can be used as an intermediate for the preparation of 6,7-dimethoxy-4-amino-2-[4-(2-furoyl)-1-piperazinyl]quinazoline (Prazosin), which possesses antihypertensive activity. <IMAGE>

Description

Изобретение относится к способу получения 3,4-диметокси-6-(4-)2-фуроил)-1-пиперазинилтиокарбамидо)бензонитрила, который может быть использован в качестве промежуточного продук- < та в синтезе биологически активного 6,7-Диметокси-4-амино- 2-/4- 2-фуройл)-1-пиперазинил) хиназолина.The invention relates to a method for producing 3,4-dimethoxy-6- (4-) 2-furoyl) -1-piperazinylthiocarbamido) benzonitrile, which can be used as an intermediate in the synthesis of biologically active 6,7 - Dimethoxy-4 amino-2- / 4- 2-furyl) -1-piperazinyl) quinazoline.

Известны методы получения изотио- ю цианатов взаимодействием аминопроизводных с тиофосгеном и реакции изотиоцианатов с аминами с образованием смешанных мочевин [1 ].Known methods for producing isothiocyanates by the interaction of amino derivatives with thiophosgene and the reaction of isothiocyanates with amines with the formation of mixed ureas [1].

Целью изобретения является основанный на известных методах способ получения 3>4-диметокси-6-(4-)2-фуро* ил)-1-пиперазинилтиокарбамидо)бензонитрила, который может быть исполь- 20 зован в синтезе известных биологических активных соединений.An object of the invention is a method based on known methods for the production of 3> 4-dimethoxy-6- (4-) 2-furo * yl) -1-piperazinylthiocarbamido) benzonitrile, which can be used in the synthesis of known biological active compounds.

Поставленная цель достигается тем, что согласно способу получения 3,4-диметокси-6-(4-(2-фуроил)-1-пиперазинилтиокарбамидо)бензонитрила формулыThis goal is achieved in that according to the method for producing 3,4-dimethoxy-6- (4- (2-furoyl) -1-piperazinylthiocarbamido) benzonitrile of the formula

который заключается в том, что 3»4-диметокси-6-аминобензонитрил формулыwhich is that 3 "4-dimethoxy-6-aminobenzonitrile of the formula

СН30 С N подвергают взаимодействию с тиофосгеном с образованием 3,4-диметокси-6-изотиоцианатобензонитрила формулы с последующим взаимодействием полученного продукта с 1-(2-фуроил)пиперазином формулыCH 3 0 C N is reacted with thiophosgene to form 3,4-dimethoxy-6-isothiocyanatobenzonitrile of the formula followed by reaction of the obtained product with 1- (2-furoyl) piperazine of the formula

1'5)1'5)

Пример 1 , Получение 3,4-диметокси-6-изотиоцианатобензонитрила (I I I).Example 1 Preparation of 3,4-Dimethoxy-6-isothiocyanatobenzonitrile (I I I).

В 150 мл 1,2-дихлорэтана растворяют 27,0 г (0,15 моль) 3,4-диметоксй-6-аминобензонитрила (II) и раствор постепенно добавляют при 0~5°С к смеси, которая содержит 23,0 г (0,2 моль) тиофосгена, 100 мл Г,2-дихлорэтана, 20,0 г (0,2 моль) карбоната кальция и 200 мл воды. После завершения добавления смесь перемешивают в течение 1 ч при 35°С. Реакционную смесь фильтруют, отделяют дихлорэтановый слой, промывают его разбавленной хлористоводородной кислотой и водой и сушат с MgS04. Растворитель удаляют в вакууме и кристаллический остаток (т.пл. 12б-127°С) используют для проведения следующей стадии. Выход составляет 31,0 г (94% от теоретического) 3,4-диметокси-6-изотиоцианатобензонитрила.27.0 g (0.15 mol) of 3,4-dimethoxy-6-aminobenzonitrile (II) is dissolved in 150 ml of 1,2-dichloroethane, and the solution is gradually added at 0 ~ 5 ° C to a mixture that contains 23.0 g (0.2 mol) of thiophosgene, 100 ml of G, 2-dichloroethane, 20.0 g (0.2 mol) of calcium carbonate and 200 ml of water. After complete addition, the mixture is stirred for 1 h at 35 ° C. The reaction mixture was filtered, the dichloroethane layer was separated, washed with dilute hydrochloric acid and water, and dried with MgS0 4 . The solvent was removed in vacuo and the crystalline residue (mp. 12b-127 ° C) was used to carry out the next step. The yield is 31.0 g (94% of theory) of 3,4-dimethoxy-6-isothiocyanatobenzonitrile.

Найдено, %: С 53,48; Н 3,78; N 12,18; S 13,79.Found,%: C 53.48; H 3.78; N, 12.18; S 13.79.

C^NqOqS.C ^ NqOqS.

Рассчитано, />'. С 54,53; Н 3,65; N 12,72; S 14,56.It is calculated, /> '. C 54.53; H 3.65; N, 12.72; S 14.56.

Пример 2. Получение 3,4-диметокси-6-(4-(2-фуроил)-1-пиперазинилтиокарбамидо)бензонитрила (1).Example 2. Obtaining 3,4-dimethoxy-6- (4- (2-furoyl) -1-piperazinylthiocarbamido) benzonitrile (1).

В 65 мл этилацетата растворяют 11,2 г (0,051 моль) 3,4-диметркси-6-изотиоцианатобензонитрила (Ш) и раствор постепенно добавляют при перемешивании и 0°С к раствору, который содержит 9,2 г (0,051 моль) 1-(2-фуроил)-пиперазина (1У) в 65 мл этилацетата. Раствор оставляют стоять , на ночь при 25°С, в результате чего продукт выкристаллизовывают. Его отфильтровывают и кристаллы промывают . 45 холодным этилацетатом и сушат. Выход составляет 16,3 г (80% теоретического) 3,4-диметокси-6-(4-)2-фуроил)-1-пи1011.2 g (0.051 mol) of 3,4-dimethoxy-6-isothiocyanatobenzonitrile (III) are dissolved in 65 ml of ethyl acetate, and the solution is gradually added with stirring and 0 ° C to a solution that contains 9.2 g (0.051 mol) 1- (2-furoyl) piperazine (1U) in 65 ml of ethyl acetate. The solution was left to stand overnight at 25 ° C, whereby the product crystallized. It is filtered off and the crystals are washed. 45 with cold ethyl acetate and dried. The yield is 16.3 g (80% of theory) of 3,4-dimethoxy-6- (4-) 2-furoyl) -1-pi10

923370 4 перазинилтиокарбамидо)бензонитрила. Т.пл. 178-180°С.923370 4 perazinylthiocarbamido) benzonitrile. Mp 178-180 ° C.

Найдено, %: С 57,4.1 ; Н 5,39; 14,14; S 7,68.Found,%: C 57.4.1; H 5.39; 14.14; S 7.68.

О4 S·O4 S

Рассчитано, %: С 56,99; Н 5,03; 13,99;-S 8,01.Calculated,%: C 56.99; H 5.03; 13.99; -S 8.01.

Claims (1)

Формула изобретенияClaim Способ получения 3,4-диметокси-6-(4-(2-фуроил)-1-пиперазинилтиокарбамидо)бензонитрила формулыThe method of obtaining 3,4-dimethoxy-6- (4- (2-furoyl) -1-piperazinylthiocarbamido) benzonitrile of the formula ГЛGL CHjOChjo NH-C-N.NH-C-N. СКSC CHjO отличающ ' 3,4-диме токси - 6формулы (II) [ИЙCHjO Featuring '3,4-Dime Toxins - 6 Formulas (II) [II -аминобензонитрил с я тем, что подвергают взаимодействию с тиофосгеном с образованием 3,4-диметокси“6-изотиоцианатобензонитрила формулы (III) сняо взаимодействием пблус последующим ченного продукта с 1-(2-фуроил)пиперазином формулы (IV) ί-aminobenzonitril with I that is reacted with thiophosgene to form 3,4-dimethoxy "6 izotiotsianatobenzonitrila of formula (III) by reaction of I cN pblus followed chennogo product 1- (2-furoyl) piperazine of formula (IV) ί Λ .Λ.
SU772555751A 1976-12-15 1977-12-14 Process for producing 3,4-dimethoxy-6-(4-(2-furoyl)-1-piperazinylthiocarbamido) benzonitrile SU923370A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FI763614A FI58124C (en) 1976-12-15 1976-12-15 NY MELLANPROTUKT 3,4-DIMETOXY-6- (4- (2-FUROYL) -1-PIPERAZINYLTHOUREA) -BENONITRIL FOR FRAMSTAELLNING AV 6,7-DIMETOXY-4-AMINO-2- (4- (2-FUROYL) -1 -PIPERAZINYL) QUINAZOLINE WITH BLODTRYCKSSAENKANDE VERKAN

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JP (1) JPS5387375A (en)
AT (1) AT358047B (en)
BE (1) BE861822A (en)
CA (1) CA1102332A (en)
CH (1) CH630624A5 (en)
CS (1) CS197312B2 (en)
DD (1) DD134226A1 (en)
DE (1) DE2755638A1 (en)
DK (1) DK145822C (en)
FI (1) FI58124C (en)
HU (1) HU174048B (en)
NL (1) NL7713703A (en)
NO (1) NO146239C (en)
PL (1) PL106201B1 (en)
SE (1) SE424993B (en)
SU (1) SU923370A3 (en)
ZA (1) ZA777222B (en)

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* Cited by examiner, † Cited by third party
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FI67699C (en) * 1979-01-31 1985-05-10 Orion Yhtymae Oy PROCEDURE FOR THE FRAMSTATION OF AV 6,7-DIMETOXY-4-AMINO-2- (4- (2-FUROYL) -1-PIPERAZINYL) QUINAZOLINE HYDROCHLORIDE WITH BLODTRYCKSSAENKANDE VERKAN

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* Cited by examiner, † Cited by third party
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US3935213A (en) * 1973-12-05 1976-01-27 Pfizer Inc. Process for hypotensive 4-amino-2-(piperazin-1-yl) quinazoline derivatives

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JPS5387375A (en) 1978-08-01
DE2755638A1 (en) 1978-06-22
DD134226A1 (en) 1979-02-14
DK558377A (en) 1978-06-16
CA1102332A (en) 1981-06-02
ATA867177A (en) 1980-01-15
BE861822A (en) 1978-03-31
PL202898A1 (en) 1978-08-28
DK145822C (en) 1983-08-29
NO774263L (en) 1978-06-16
FI58124B (en) 1980-08-29
PL106201B1 (en) 1979-12-31
NO146239B (en) 1982-05-18
CH630624A5 (en) 1982-06-30
NL7713703A (en) 1978-06-19
ZA777222B (en) 1978-09-27
SE7713377L (en) 1978-06-16
AT358047B (en) 1980-08-11
SE424993B (en) 1982-08-23
DK145822B (en) 1983-03-14
CS197312B2 (en) 1980-04-30
FI58124C (en) 1980-12-10
NO146239C (en) 1982-08-25
HU174048B (en) 1979-10-28
JPS6225145B2 (en) 1987-06-01
FI763614A (en) 1978-06-16

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