SU799657A3 - Method of preparing 3,5-diphenylpyrazole - Google Patents

Method of preparing 3,5-diphenylpyrazole Download PDF

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Publication number
SU799657A3
SU799657A3 SU762319859A SU2319859A SU799657A3 SU 799657 A3 SU799657 A3 SU 799657A3 SU 762319859 A SU762319859 A SU 762319859A SU 2319859 A SU2319859 A SU 2319859A SU 799657 A3 SU799657 A3 SU 799657A3
Authority
SU
USSR - Soviet Union
Prior art keywords
palladium
diphenyl
reaction mixture
pyrazolines
diphenylpyrazole
Prior art date
Application number
SU762319859A
Other languages
Russian (ru)
Inventor
Гарбер Мюррей
Джеймс Росс Лоренс
Джозеф Степек Уолтер
Original Assignee
Американ Цианамид Компани (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
Priority claimed from US05/549,219 external-priority patent/US3952010A/en
Application filed by Американ Цианамид Компани (Фирма) filed Critical Американ Цианамид Компани (Фирма)
Application granted granted Critical
Publication of SU799657A3 publication Critical patent/SU799657A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

3,5-Diphenylpyrazole, 3,5-diphenyl-4-alkylpyrazoles or 3,5-diphenyl-4-alkoxypyrazoles are prepared from the corresponding pyrazolines by catalytic dehydrogenation in an inert organic solvent. Platinum or palladium, both of which can also be supported by various substances, can be used as catalysts. The pyrazolines used as starting material can be obtained by reacting a methyl ketone, such as acetophenone or its derivatives, with a suitable aldehyde, such as benzaldehyde, in the presence of a base, to give a 1,3-disubstituted alpha , beta -unsaturated ketone, such as chalcone or its substitution products, acidification of the resulting reaction mixture and treatment of the acidified reaction mixture with hydrazine. The compounds prepared according to the invention can be used as starting substances for the preparation of corresponding 3,5-disubstituted 1,2-dialkylpyrazolium salts, such as 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulphate which, in turn, can be used as herbicides.

Description

(54) СПОСОБ ПОЛУЧЕНИЯ 3,5-ДИФЕНИЛПИРАЗОЛА(54) METHOD FOR OBTAINING 3,5-DIPHENYLPIRAZOL

в качестве катализатора примен ют 0,4 ч.паллсщиевой черни (ю О % Pd) . . После кип чени  в течение 4 ч удап ют непрорёагировашшй 3,5-дифенил-2-1шраэолин в количестве 1,1% и получают -3,5-дифенилпиразол, плав дийс  при 197-2G1 С. Выход 88,9%,0.4 parts of mobile black (UO% Pd) is used as a catalyst. . After boiling for 4 hours, unreacted 3,5-diphenyl-2-1shraeolin in the amount of 1.1% yields -3,5-diphenylpyrazole, melting at 197-2G1 C. Yield 88.9%,

формула изобретени invention formula

Способ получени  3,5-дифенилпиравола путем дегидрировани  3,5-дифеиилпиразолина в среде органическогоThe method of obtaining 3,5-diphenylpyravol by dehydrogenating 3,5-dipheiylpyrazoline in organic medium

растворител  при температуре кипени  в присутствии катализатора дегидрировани , отличающийс  тем, что с целью повышени  выхода цепевого продукта, в качестве катализатора дегидрировани  примен ют палладиевую чернь или палладий на окиси алюмини  или палладий на сульфате бари .solvent at boiling point in the presence of a dehydrogenation catalyst, characterized in that in order to increase the yield of the chain product, palladium black or palladium on alumina or palladium on barium sulfate is used as a catalyst for dehydrogenation.

Источники информации,Information sources,

прин тые во внимание при экспертизеtaken into account in the examination

1. Патент СССР I 645567, кл. С 07 D 213/12, 1974(прототип).1. Patent of the USSR I 645567, cl. C 07 D 213/12, 1974 (prototype).

Claims (1)

Формула изобретенияClaim Способ получения 3,5-дифенилпиравола путем дегидрирования 3,5-дифенилпиразолина в среде органическогоThe method of obtaining 3,5-diphenylpyravolum by dehydrogenation of 3,5-diphenylpyrazoline in an organic medium 799657 4 •растворителя при температуре кипения в присутствии катализатора дегидрирования, отличающийся тем, что с целью повышения выхода це левого продукта, в качестве катали- затора дегидрирования применяют палладиевую чернь или палладий на окиси алюминия или палладий на сульфате бария .799657 4 • solvent at the boiling point in the presence of a dehydrogenation catalyst, characterized in that in order to increase the yield of the target product, palladium black or palladium on alumina or palladium on barium sulfate is used as a dehydrogenation catalyst. Q Источники информации, принятые во внимание при экспертизе 1. Патент СССР № 645567, кл. С 07 D 213/12, 1974(прототип).Q Sources of information taken into account during the examination 1. USSR patent No. 645567, cl. C 07 D 213/12, 1974 (prototype). Составитель Ж. Сергеева Compiled by J. Sergeev Редактор М. Ликович Заказ 10106/87 Editor M. Likovich Order 10106/87 Техред Ж. Кастелевич корректор ,Н. Швыдкая Тираж 454 Подписное Tehred J. Kastelevich proofreader, N. Shydkoy Circulation 454 Subscription
ВНИИПИ Государственного комитета СССР по делам изобретений и открытийVNIIIPI of the USSR State Committee for Inventions and Discoveries 113035, Москва, Ж-35, Раушская наб,, д. 4/5113035, Moscow, Zh-35, Raushskaya embankment, d. 4/5 Филиал ППП Патент,г. Ужгород, ул. Проектная,4Branch of PPP Patent Uzhhorod, st. Project, 4
SU762319859A 1975-02-12 1976-02-11 Method of preparing 3,5-diphenylpyrazole SU799657A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/549,219 US3952010A (en) 1973-09-17 1975-02-12 Catalytic dehydrogenation process for the preparation of 3,5-disubstituted pyrazoles

Publications (1)

Publication Number Publication Date
SU799657A3 true SU799657A3 (en) 1981-01-23

Family

ID=24192112

Family Applications (1)

Application Number Title Priority Date Filing Date
SU762319859A SU799657A3 (en) 1975-02-12 1976-02-11 Method of preparing 3,5-diphenylpyrazole

Country Status (19)

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JP (2) JPS51101979A (en)
AT (1) AT350549B (en)
BE (1) BE838408R (en)
BR (1) BR7600847A (en)
CA (1) CA1060455A (en)
CH (1) CH608004A5 (en)
CS (1) CS192554B2 (en)
DD (1) DD124249A6 (en)
DE (1) DE2602965A1 (en)
DK (1) DK55276A (en)
ES (1) ES445094A2 (en)
FR (1) FR2300763A2 (en)
GB (1) GB1537859A (en)
IL (1) IL48724A (en)
IT (1) IT1053296B (en)
NL (1) NL178075C (en)
SE (1) SE7601544L (en)
SU (1) SU799657A3 (en)
ZA (1) ZA757986B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3029160A1 (en) * 1980-08-01 1982-03-04 Basf Ag, 6700 Ludwigshafen METHOD FOR PRODUCING PYRAZOLES

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5855148A (en) * 1981-09-29 1983-04-01 Hino Motors Ltd Production of die for molding

Also Published As

Publication number Publication date
IL48724A (en) 1979-07-25
FR2300763A2 (en) 1976-09-10
DD124249A6 (en) 1977-02-09
CH608004A5 (en) 1978-12-15
IT1053296B (en) 1981-08-31
AT350549B (en) 1979-06-11
CA1060455A (en) 1979-08-14
AU8790475A (en) 1977-06-30
FR2300763B2 (en) 1982-09-03
ATA96276A (en) 1978-11-15
IL48724A0 (en) 1976-02-29
NL178075C (en) 1986-01-16
NL7600445A (en) 1976-08-16
BR7600847A (en) 1976-09-14
DE2602965A1 (en) 1976-08-26
CS192554B2 (en) 1979-08-31
BE838408R (en) 1976-08-10
ES445094A2 (en) 1977-06-16
ZA757986B (en) 1976-12-29
JPS6227068B2 (en) 1987-06-12
DK55276A (en) 1976-08-13
NL178075B (en) 1985-08-16
GB1537859A (en) 1979-01-04
DE2602965C2 (en) 1988-11-17
SE7601544L (en) 1976-08-13
JPS51101979A (en) 1976-09-08
JPS60222463A (en) 1985-11-07

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