JPS6118780A - １ｈ−ピラゾロ〔３，２−ｃ〕−ｓ−トリアゾール系化合物の製造方法 - Google Patents

１ｈ−ピラゾロ〔３，２−ｃ〕−ｓ−トリアゾール系化合物の製造方法

Info

Publication number: JPS6118780A
Authority: JP; Japan
Prior art keywords: pyrazolo; acid; triazole; compound; based compound
Prior art date: 1984-07-06
Legal status (The legal status 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 status listed.): Granted

Application number

JP14024884A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0420437B2 (da

Inventor

Hisashi Ishikawa

恒石川

Satoshi Nakagawa

敏仲川

Kaoru Miyagi

薫宮城

Satoru Kawakatsu

川勝　哲

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Konica Minolta Inc

Original Assignee

Konica Minolta Inc

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.)

1984-07-06

Filing date

1984-07-06

Publication date

1986-01-27

1984-07-06 Application filed by Konica Minolta Inc filed Critical Konica Minolta Inc

1984-07-06 Priority to JP14024884A priority Critical patent/JPS6118780A/ja

1986-01-27 Publication of JPS6118780A publication Critical patent/JPS6118780A/ja

1992-04-02 Publication of JPH0420437B2 publication Critical patent/JPH0420437B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title abstract description 22
UDFSJHJKINSRFV-UHFFFAOYSA-N N1N=CN2N=CC=C21 Chemical compound N1N=CN2N=CC=C21 UDFSJHJKINSRFV-UHFFFAOYSA-N 0.000 title 1
239000002253 acid Substances 0.000 claims abstract description 15
239000002904 solvent Substances 0.000 claims abstract description 9
238000009835 boiling Methods 0.000 claims abstract description 3
150000001735 carboxylic acids Chemical class 0.000 claims abstract description 3
GNVFDZCGEHLUDH-UHFFFAOYSA-N OC(C1=C(NN=C2)N2N=C1)=O Chemical compound OC(C1=C(NN=C2)N2N=C1)=O GNVFDZCGEHLUDH-UHFFFAOYSA-N 0.000 claims abstract 3
-1 1H-pyrazolo[3,2-C]-S-triazole compound Chemical class 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 9
125000000217 alkyl group Chemical group 0.000 abstract description 9
238000000034 method Methods 0.000 abstract description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 7
125000003118 aryl group Chemical group 0.000 abstract description 5
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract description 4
125000001424 substituent group Chemical group 0.000 abstract description 4
125000000623 heterocyclic group Chemical group 0.000 abstract description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract description 2
235000019253 formic acid Nutrition 0.000 abstract description 2
239000002994 raw material Substances 0.000 abstract description 2
235000011149 sulphuric acid Nutrition 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001914 filtration Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
239000005457 ice water Substances 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical group COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229940000488 arsenic acid Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
RMGVZKRVHHSUIM-UHFFFAOYSA-N dithionic acid Chemical compound OS(=O)(=O)S(O)(=O)=O RMGVZKRVHHSUIM-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical compound O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)

JP14024884A 1984-07-06 1984-07-06 １ｈ−ピラゾロ〔３，２−ｃ〕−ｓ−トリアゾール系化合物の製造方法 Granted JPS6118780A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP14024884A JPS6118780A (ja)	1984-07-06	1984-07-06	１ｈ−ピラゾロ〔３，２−ｃ〕−ｓ−トリアゾール系化合物の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP14024884A JPS6118780A (ja)	1984-07-06	1984-07-06	１ｈ−ピラゾロ〔３，２−ｃ〕−ｓ−トリアゾール系化合物の製造方法

Publications (2)

Publication Number	Publication Date
JPS6118780A true JPS6118780A (ja)	1986-01-27
JPH0420437B2 JPH0420437B2 (da)	1992-04-02

Family

ID=15264356

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP14024884A Granted JPS6118780A (ja)	1984-07-06	1984-07-06	１ｈ−ピラゾロ〔３，２−ｃ〕−ｓ−トリアゾール系化合物の製造方法

Country Status (1)

Country	Link
JP (1)	JPS6118780A (da)

1984
- 1984-07-06 JP JP14024884A patent/JPS6118780A/ja active Granted

Also Published As

Publication number	Publication date
JPH0420437B2 (da)	1992-04-02

Publication	Publication Date	Title
JPH02256647A (ja)	1990-10-17	２，４―ジヒドロキシ安息香酸の製造方法
JP3268825B2 (ja)	2002-03-25	３−クロロアントラニル酸アルキルの製造方法
DE1695702C3 (de)	1974-01-17	Verfahren zur Herstellung von 1-Acyl-2-carboxy-3-indolylessigsäuren
JPH03123762A (ja)	1991-05-27	２，４‐または２，６‐ジハロゲノアニリンの製法
JPH03167144A (ja)	1991-07-19	フルオロベンゼンの製造方法
JPH0420437B2 (da)	1992-04-02
JPH06192170A (ja)	1994-07-12	４−ブロモメチルビフェニル化合物の製造法
JP3013528B2 (ja)	2000-02-28	２−ニトロ−４，６− ジクロロ−５− メチルフェノールの精製方法
JPH01160804A (ja)	1989-06-23	一塩化沃素の製造方法
JPS62292771A (ja)	1987-12-19	ベンゾグアナミン誘導体の製法
SU1143745A1 (ru)	1985-03-07	Способ получени производных 3-(3-бензоксазолонил)пропановой кислоты
JP2717995B2 (ja)	1998-02-25	１，２，３−トリアゾールの製法
JP2018076289A (ja)	2018-05-17	ハロゲン化ベンゼン誘導体の製造方法
JPH01242537A (ja)	1989-09-27	２−フルオロビフェニル誘導体の製造方法
JP5008796B2 (ja)	2012-08-22	芳香族カルボン酸の製造方法
US6242646B1 (en)	2001-06-05	Method of producing 2,4-dichloro-5-hydroxyacetanilide
JPH03236361A (ja)	1991-10-22	２−アシルアミノ桂皮酸誘導体の製造法
JP2000128827A (ja)	2000-05-09	ヒドロキシ安息香酸類の製造方法
JPH029572B2 (da)	1990-03-02
JPH1180128A (ja)	1999-03-26	５，６−ジアミノ−１，３−ジ−（２−プロペニル）ウラシルの精製安定化方法
JPH0378379B2 (da)	1991-12-13
JPS5850993B2 (ja)	1983-11-14	４↓−アルコキシカルボニル↓−３，５↓−ジメチルフタル酸無水物の製造方法
JPH09216854A (ja)	1997-08-19	３−クロロ−３’−ニトロ−４’−メトキシベンゾフエノンの製造方法
US20050143607A1 (en)	2005-06-30	Method for the preparation of alpha, alpha, alpha', alpha'-tetrachloro-p-xylene
JP2008001663A (ja)	2008-01-10	２−クロロアニリン化合物の製造方法