CS244848B2 - Production method of 1-alkyl-3,5-diphenylpyrazole - Google Patents

Production method of 1-alkyl-3,5-diphenylpyrazole Download PDF

Info

Publication number: CS244848B2
Authority: CS; Czechoslovakia
Prior art keywords: alkyl; carbon atoms; reaction; sulfate; formula
Prior art date: 1984-03-05

Application number

CS851134A

Other languages

Czech (cs)

English (en)

Inventor

Dohnal R Maulding

Original Assignee

American Cyanamid Co

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.)

1984-03-05

Filing date

1985-02-18

Publication date

1986-08-14

1985-02-18 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1986-08-14 Publication of CS244848B2 publication Critical patent/CS244848B2/cs

Links

238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 25
239000003444 phase transfer catalyst Substances 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 11
150000008050 dialkyl sulfates Chemical class 0.000 claims abstract description 5
125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 12
239000008096 xylene Substances 0.000 claims description 12
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 11
-1 alkoxybenzene sulfonate Chemical class 0.000 claims description 8
239000002585 base Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
239000002168 alkylating agent Substances 0.000 claims description 4
229940100198 alkylating agent Drugs 0.000 claims description 4
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 2
229940117389 dichlorobenzene Drugs 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical group [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims 2
125000001188 haloalkyl group Chemical group 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 claims 1
229910019142 PO4 Inorganic materials 0.000 claims 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
229940077388 benzenesulfonate Drugs 0.000 claims 1
150000001649 bromium compounds Chemical group 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical group COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 claims 1
150000004028 organic sulfates Chemical class 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
239000010452 phosphate Substances 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract description 2
229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
239000004305 biphenyl Substances 0.000 abstract 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
SVDTUJAQNAQGGW-UHFFFAOYSA-N 1-methyl-3,5-diphenylpyrazole Chemical compound CN1N=C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 SVDTUJAQNAQGGW-UHFFFAOYSA-N 0.000 description 4
JXHKUYQCEJILEI-UHFFFAOYSA-N 3,5-diphenyl-1h-pyrazole Chemical class C=1C(C=2C=CC=CC=2)=NNC=1C1=CC=CC=C1 JXHKUYQCEJILEI-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
SQZBSJYCKXPFPI-UHFFFAOYSA-N 3-methyl-1,4-diphenyl-2H-triazole Chemical compound C1(=CC=CC=C1)N1NN(C(=C1)C1=CC=CC=C1)C SQZBSJYCKXPFPI-UHFFFAOYSA-N 0.000 description 1
OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
206010011878 Deafness Diseases 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
241000209140 Triticum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000003851 azoles Chemical class 0.000 description 1
YGVJSKQNZUYONI-UHFFFAOYSA-N benzyl(tert-butyl)azanium;chloride Chemical compound [Cl-].CC(C)(C)[NH2+]CC1=CC=CC=C1 YGVJSKQNZUYONI-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

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
- C07D231/10—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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CS851134A 1984-03-05 1985-02-18 Production method of 1-alkyl-3,5-diphenylpyrazole CS244848B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US58594984A	1984-03-05	1984-03-05

Publications (1)

Publication Number	Publication Date
CS244848B2 true CS244848B2 (en)	1986-08-14

Family

ID=24343672

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS851134A CS244848B2 (en)	1984-03-05	1985-02-18	Production method of 1-alkyl-3,5-diphenylpyrazole

Country Status (12)

Country	Link
EP (1)	EP0155492B1 (de)
JP (1)	JPS60204766A (de)
AT (1)	ATE48599T1 (de)
AU (1)	AU569609B2 (de)
BR (1)	BR8500961A (de)
CA (1)	CA1238641A (de)
CS (1)	CS244848B2 (de)
DD (1)	DD232040A5 (de)
DE (1)	DE3506972A1 (de)
DK (1)	DK163122C (de)
IL (1)	IL74429A (de)
ZA (1)	ZA851623B (de)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4146721A (en) *	1969-09-12	1979-03-27	Byk Gulden Lomberg Chemische Fabrik Gmbh	Pyrazol-4-acetic acid compounds
US3907824A (en) *	1973-06-18	1975-09-23	American Cyanamid Co	Preparation of 1-alkyl-3,5-diphenylpyrazoles and 1,2-dialkyl-3,5-diphenylpyrazolium salts

1985
- 1985-02-09 AT AT85101392T patent/ATE48599T1/de not_active IP Right Cessation
- 1985-02-09 EP EP85101392A patent/EP0155492B1/de not_active Expired
- 1985-02-18 CS CS851134A patent/CS244848B2/cs unknown
- 1985-02-24 IL IL74429A patent/IL74429A/xx unknown
- 1985-02-27 DE DE19853506972 patent/DE3506972A1/de not_active Ceased
- 1985-03-01 DD DD85273694A patent/DD232040A5/de not_active IP Right Cessation
- 1985-03-01 CA CA000475533A patent/CA1238641A/en not_active Expired
- 1985-03-01 JP JP60039010A patent/JPS60204766A/ja active Granted
- 1985-03-04 BR BR8500961A patent/BR8500961A/pt not_active IP Right Cessation
- 1985-03-04 AU AU39440/85A patent/AU569609B2/en not_active Ceased
- 1985-03-04 DK DK099285A patent/DK163122C/da not_active IP Right Cessation
- 1985-03-04 ZA ZA851623A patent/ZA851623B/xx unknown

Also Published As

Publication number	Publication date
DK99285A (da)	1985-09-06
EP0155492A1 (de)	1985-09-25
DD232040A5 (de)	1986-01-15
ZA851623B (en)	1985-10-30
JPS60204766A (ja)	1985-10-16
BR8500961A (pt)	1985-10-22
EP0155492B1 (de)	1989-12-13
IL74429A0 (en)	1985-05-31
JPH0568467B2 (de)	1993-09-29
IL74429A (en)	1988-09-30
AU569609B2 (en)	1988-02-11
DK99285D0 (da)	1985-03-04
DK163122B (da)	1992-01-20
AU3944085A (en)	1985-09-12
DE3506972A1 (de)	1985-09-05
CA1238641A (en)	1988-06-28
DK163122C (da)	1992-06-09
ATE48599T1 (de)	1989-12-15

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