SK19452000A3 - Spsob dehalogencie derivtov tiochrmanu a dihydrobenzotiofnu - Google Patents

Spsob dehalogencie derivtov tiochrmanu a dihydrobenzotiofnu Download PDF

Info

Publication number: SK19452000A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; alkyl; independently; represent
Prior art date: 1999-04-06

Application number

SK1945-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Thomas Walter Drabb Jr.

Original Assignee

American Cyanamid Company

Idemitsu Kosan Co., Ltd.

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.)

1999-04-06

Filing date

2000-03-14

Publication date

2001-09-11

2000-03-14 Application filed by American Cyanamid Company, Idemitsu Kosan Co., Ltd. filed Critical American Cyanamid Company

2001-09-11 Publication of SK19452000A3 publication Critical patent/SK19452000A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 33
230000008569 process Effects 0.000 title claims abstract description 19
238000005695 dehalogenation reaction Methods 0.000 title abstract description 4
YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical class C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 title description 6
WPWNEKFMGCWNPR-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene Chemical compound C1=CC=C2CCCSC2=C1 WPWNEKFMGCWNPR-UHFFFAOYSA-N 0.000 title description 4
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052723 transition metal Inorganic materials 0.000 claims abstract description 9
150000003624 transition metals Chemical class 0.000 claims abstract description 9
239000003054 catalyst Substances 0.000 claims abstract description 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 14
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
230000002363 herbicidal effect Effects 0.000 claims description 9
239000002798 polar solvent Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 5
230000003197 catalytic effect Effects 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
238000006243 chemical reaction Methods 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
239000012065 filter cake Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 4
-1 hydroxypyrazolyl compound Chemical class 0.000 description 4
238000010992 reflux Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
125000005129 aryl carbonyl group Chemical group 0.000 description 2
238000010586 diagram Methods 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
WBCNOHSYFWGZGJ-UHFFFAOYSA-N 1,1-dioxothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1(=O)=O WBCNOHSYFWGZGJ-UHFFFAOYSA-N 0.000 description 1
NTKNWYOHHBSWLL-UHFFFAOYSA-N 3,3,4-trimethyl-2h-1-benzothiophene-5-carboxylic acid Chemical compound C1=C(C(O)=O)C(C)=C2C(C)(C)CSC2=C1 NTKNWYOHHBSWLL-UHFFFAOYSA-N 0.000 description 1
KZNXLZCMWSZLTJ-UHFFFAOYSA-N 7-chloro-3,3,4-trimethyl-2h-1-benzothiophene-5-carboxylic acid Chemical compound C1=C(C(O)=O)C(C)=C2C(C)(C)CSC2=C1Cl KZNXLZCMWSZLTJ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
VGTMRZJCMCTKMG-UHFFFAOYSA-N ethyl 2,3-dihydro-1-benzothiophene-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2SCCC2=C1 VGTMRZJCMCTKMG-UHFFFAOYSA-N 0.000 description 1
CHYUBRROXLQLFX-UHFFFAOYSA-N ethyl 3,4-dihydro-2h-thiochromene-6-carboxylate Chemical compound S1CCCC2=CC(C(=O)OCC)=CC=C21 CHYUBRROXLQLFX-UHFFFAOYSA-N 0.000 description 1
NMJDJFWCAWXLFM-UHFFFAOYSA-N ethyl 5-methyl-4-oxo-2,3-dihydrothiochromene-6-carboxylate Chemical compound S1CCC(=O)C2=C(C)C(C(=O)OCC)=CC=C21 NMJDJFWCAWXLFM-UHFFFAOYSA-N 0.000 description 1
IJRSFXONLHDFNO-UHFFFAOYSA-N ethyl 8-chloro-5-methyl-4-oxo-2,3-dihydrothiochromene-6-carboxylate Chemical compound S1CCC(=O)C2=C(C)C(C(=O)OCC)=CC(Cl)=C21 IJRSFXONLHDFNO-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Catalysts (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

SK1945-2000A 1999-04-06 2000-03-14 Spsob dehalogencie derivtov tiochrmanu a dihydrobenzotiofnu SK19452000A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US28686799A	1999-04-06	1999-04-06
PCT/US2000/006601 WO2000059898A2 (en)	1999-04-06	2000-03-14	Process for the dehalogenation of thiochroman and dihydrobenzothiophene derivatives

Publications (1)

Publication Number	Publication Date
SK19452000A3 true SK19452000A3 (sk)	2001-09-11

Family

ID=23100514

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1945-2000A SK19452000A3 (sk)	1999-04-06	2000-03-14	Spsob dehalogencie derivtov tiochrmanu a dihydrobenzotiofnu

Country Status (18)

Country	Link
EP (1)	EP1044973B1 (ru)
JP (1)	JP2002541149A (ru)
KR (1)	KR20010071408A (ru)
CN (1)	CN1310717A (ru)
AR (1)	AR029746A1 (ru)
AT (1)	ATE251620T1 (ru)
AU (1)	AU3881500A (ru)
BR (1)	BR0006017A (ru)
CA (1)	CA2334478A1 (ru)
CZ (1)	CZ200150A3 (ru)
DE (1)	DE60005734D1 (ru)
EA (1)	EA200100017A1 (ru)
HU (1)	HUP0102649A3 (ru)
IL (1)	IL139830A0 (ru)
PL (1)	PL344666A1 (ru)
SK (1)	SK19452000A3 (ru)
UA (1)	UA58599C2 (ru)
WO (1)	WO2000059898A2 (ru)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN119876973B (zh) *	2023-10-25	2025-10-10	安阳工学院	一种2,3-二氢苯并氧化噻吩类化合物的电化学制备方法与应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5607898A (en) *	1993-08-02	1997-03-04	Idemitsu Kosan Company, Ltd.	Pyrazole derivatives
US5420295A (en) *	1994-01-19	1995-05-30	Allergan, Inc.	Process for preparing 4,4-dialkyl-6-halo-chromans or thiochromans useful as pharmaceutical intermediates

2000
- 2000-03-14 BR BR0006017-8A patent/BR0006017A/pt not_active IP Right Cessation
- 2000-03-14 UA UA2001010135A patent/UA58599C2/ru unknown
- 2000-03-14 CN CN00800514A patent/CN1310717A/zh active Pending
- 2000-03-14 PL PL00344666A patent/PL344666A1/xx not_active Application Discontinuation
- 2000-03-14 HU HU0102649A patent/HUP0102649A3/hu unknown
- 2000-03-14 IL IL13983000A patent/IL139830A0/xx unknown
- 2000-03-14 WO PCT/US2000/006601 patent/WO2000059898A2/en not_active Ceased
- 2000-03-14 AU AU38815/00A patent/AU3881500A/en not_active Abandoned
- 2000-03-14 SK SK1945-2000A patent/SK19452000A3/sk unknown
- 2000-03-14 JP JP2000609409A patent/JP2002541149A/ja active Pending
- 2000-03-14 EA EA200100017A patent/EA200100017A1/ru unknown
- 2000-03-14 CA CA002334478A patent/CA2334478A1/en not_active Abandoned
- 2000-03-14 KR KR1020007013761A patent/KR20010071408A/ko not_active Abandoned
- 2000-03-14 CZ CZ200150A patent/CZ200150A3/cs unknown
- 2000-04-05 DE DE60005734T patent/DE60005734D1/de not_active Expired - Lifetime
- 2000-04-05 AT AT00302887T patent/ATE251620T1/de not_active IP Right Cessation
- 2000-04-05 AR ARP000101561A patent/AR029746A1/es not_active Application Discontinuation
- 2000-04-05 EP EP00302887A patent/EP1044973B1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
WO2000059898A2 (en)	2000-10-12
HUP0102649A3 (en)	2002-03-28
DE60005734D1 (de)	2003-11-13
IL139830A0 (en)	2002-02-10
ATE251620T1 (de)	2003-10-15
UA58599C2 (ru)	2003-08-15
EP1044973A3 (en)	2001-01-10
EA200100017A1 (ru)	2001-08-27
EP1044973A9 (en)	2001-03-28
HUP0102649A2 (hu)	2001-11-28
KR20010071408A (ko)	2001-07-28
EP1044973B1 (en)	2003-10-08
CZ200150A3 (cs)	2002-03-13
WO2000059898A3 (en)	2001-02-08
JP2002541149A (ja)	2002-12-03
BR0006017A (pt)	2001-03-06
PL344666A1 (en)	2001-11-19
AR029746A1 (es)	2003-07-16
CA2334478A1 (en)	2000-10-12
EP1044973A2 (en)	2000-10-18
CN1310717A (zh)	2001-08-29
AU3881500A (en)	2000-10-23

Publication	Publication Date	Title
JP3478830B2 (ja)	2003-12-15	ピラゾール誘導体
DD280320A5 (de)	1990-07-04	Herstellung von zwischenprodukten der oxophthalazinyl-essigsaeuren mit benzothiazol oder anderen heterocyclischen seitenketten
JPS63192768A (ja)	1988-08-10	芳香族アミン誘導体
EP1006105A1 (en)	2000-06-07	Benzene derivatives
SK19452000A3 (sk)	2001-09-11	Spsob dehalogencie derivtov tiochrmanu a dihydrobenzotiofnu
JPH0782268A (ja)	1995-03-28	ベンゾチアジアゾール誘導体の製法
KR0140232B1 (ko)	1998-06-01	헥사히드로피리다진-1,2-디카르복시 유도체의 제조방법
US6180797B1 (en)	2001-01-30	Process for the dehalogenation of thiochroman and dihydrobenzothiophene derivatives
KR100302346B1 (ko)	2001-09-22	6-히드록시-2-옥소-1,2,3,4-테트라히드로퀴놀린의 제조방법
JP2809482B2 (ja)	1998-10-08	２―アルコキシ―１，４―ジヒドロ―４―オキソ―３―ピリジンカルボキサミド誘導体、その製造法および除草剤
JP2809483B2 (ja)	1998-10-08	６―インドリジンカルボキサミド誘導体、その中間体それらの製造法および除草剤
JP3177288B2 (ja)	2001-06-18	２−オキソ−３−ピロリン誘導体及び除草剤
JP2536756B2 (ja)	1996-09-18	５−アルコキシアントラニル酸エステル
MXPA00012029A (es)	2002-03-26	Proceso para la deshalogenacion de derivados de tiocromano y dihidrobenzotiofeno
JP3376481B2 (ja)	2003-02-10	ヘキサヒドロピリダジンの製造法
JPH05117214A (ja)	1993-05-14	ジフエニルアミン誘導体の製造法
JP2515122B2 (ja)	1996-07-10	アントラニル酸エステルの製造方法
KR20040007446A (ko)	2004-01-24	시아노티오아세트아미드 유도체 및 이의 제조 방법
EP0693482A1 (en)	1996-01-24	Process for producing hexahydropyridazine and hexahydropyridazine-1,2-dicarboxylate derivative
JPH08143536A (ja)	1996-06-04	置換ベンゼンカルボン酸誘導体およびその製造法
JPH08143538A (ja)	1996-06-04	酸アジド誘導体およびその製造法
JPH08259524A (ja)	1996-10-08	酸アジド誘導体およびその製造法
JPH1112254A (ja)	1999-01-19	３−（３−ピリジルメチルアミノ）−３，４−ジヒドロ−２（１ｈ）−キナゾリノン誘導体及びその中間体の製造方法
JPH04182460A (ja)	1992-06-30	アニリド誘導体およびその製造法
WO2001005775A1 (en)	2001-01-25	Process for the preparation of substituted benzisothiazole compounds