CA2100562A1 - Procede pour la production de 4h-3,1-benzoxazine-4-ones - Google Patents

Procede pour la production de 4h-3,1-benzoxazine-4-ones

Info

Publication number: CA2100562A1
Authority: CA; Canada
Prior art keywords: groups; alkyl; halogen; reaction; alkoxy
Prior art date: 1991-01-18
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.): Abandoned

Application number

CA002100562A

Other languages

English (en)

Inventor

Erwin Hahn

Paul Guenthert

Guenther Glas

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.)

BASF SE

Original Assignee

Individual

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.)

1991-01-18

Filing date

1992-01-08

Publication date

1992-07-19

1992-01-08 Application filed by Individual filed Critical Individual

1992-07-19 Publication of CA2100562A1 publication Critical patent/CA2100562A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 12
238000006243 chemical reaction Methods 0.000 claims abstract description 26
150000001266 acyl halides Chemical class 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 8
229910052736 halogen Chemical group 0.000 claims abstract description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 5
SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical class C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 claims abstract description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052794 bromium Chemical group 0.000 claims abstract description 5
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
239000000460 chlorine Substances 0.000 claims abstract description 5
150000002367 halogens Chemical group 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
238000002360 preparation method Methods 0.000 claims description 9
VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
-1 sulpho Chemical group 0.000 abstract description 17
125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
150000008065 acid anhydrides Chemical class 0.000 abstract 1
125000001309 chloro group Chemical group Cl* 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
HTTLBYITFHMYFK-UHFFFAOYSA-N bentranil Chemical compound N=1C2=CC=CC=C2C(=O)OC=1C1=CC=CC=C1 HTTLBYITFHMYFK-UHFFFAOYSA-N 0.000 description 3
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
239000007789 gas Substances 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000000126 substance Substances 0.000 description 3
RFQGAFQKNITSIA-UHFFFAOYSA-N 2-(carboxyamino)benzoic acid Chemical compound OC(=O)NC1=CC=CC=C1C(O)=O RFQGAFQKNITSIA-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000003599 detergent Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
HTWMTDKMOSSPMU-UHFFFAOYSA-N 1,2-benzoxazin-4-one Chemical group C1=CC=C2C(=O)C=NOC2=C1 HTWMTDKMOSSPMU-UHFFFAOYSA-N 0.000 description 1
FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
WMQSKECCMQRJRX-UHFFFAOYSA-N 2-methyl-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C)=NC2=C1 WMQSKECCMQRJRX-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000790917 Dioxys <bee> Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000012963 UV stabilizer Substances 0.000 description 1
239000012190 activator Substances 0.000 description 1
150000001262 acyl bromides Chemical class 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000005130 benzoxazines Chemical class 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
239000007844 bleaching agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CA002100562A 1991-01-18 1992-01-08 Procede pour la production de 4h-3,1-benzoxazine-4-ones Abandoned CA2100562A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19914101380 DE4101380A1 (de)	1991-01-18	1991-01-18	Verfahren zur herstellung von 4h-3,1-benzoxazin-4-onen
DEP4101380.8		1991-01-18
PCT/EP1992/000025 WO1992012971A1 (fr)	1991-01-18	1992-01-08	Procede de production de 4h-3,1-benzoxazin-4-ones

Publications (1)

Publication Number	Publication Date
CA2100562A1 true CA2100562A1 (fr)	1992-07-19

Family

ID=6423266

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002100562A Abandoned CA2100562A1 (fr)	1991-01-18	1992-01-08	Procede pour la production de 4h-3,1-benzoxazine-4-ones

Country Status (5)

Country	Link
EP (1)	EP0569377A1 (fr)
JP (1)	JPH06504532A (fr)
CA (1)	CA2100562A1 (fr)
DE (1)	DE4101380A1 (fr)
WO (1)	WO1992012971A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4134770A1 (de) *	1991-10-22	1993-04-29	Basf Ag	Koernige bleichaktivatorzusammensetzung
WO1993022300A1 (fr) *	1992-04-23	1993-11-11	Bp Chemicals Limited	Procede de production de 2-phenyl-benzoxazin-4-one
WO1997048707A1 (fr) *	1996-06-20	1997-12-24	Smithkline Beecham Plc	Derives de la 4h-3,1-benzoxazin-4-one et analogues utilises comme agents antiviraux
US6774232B2 (en) *	2001-10-22	2004-08-10	Cytec Technology Corp.	Low color, low sodium benzoxazinone UV absorbers and process for making same
CN115043782B (zh) *	2022-06-01	2023-08-08	贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室)	4h-3,1-苯并噁嗪-4-酮衍生物及其制备方法和应用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3514183A1 (de) *	1985-04-19	1986-10-23	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung substituierter 2-phenyl-4h-3,1-benzoxazin-4-one

1991
- 1991-01-18 DE DE19914101380 patent/DE4101380A1/de not_active Withdrawn
1992
- 1992-01-08 CA CA002100562A patent/CA2100562A1/fr not_active Abandoned
- 1992-01-08 EP EP19920901610 patent/EP0569377A1/fr not_active Withdrawn
- 1992-01-08 WO PCT/EP1992/000025 patent/WO1992012971A1/fr not_active Ceased
- 1992-01-08 JP JP4502084A patent/JPH06504532A/ja active Pending

Also Published As

Publication number	Publication date
EP0569377A1 (fr)	1993-11-18
WO1992012971A1 (fr)	1992-08-06
JPH06504532A (ja)	1994-05-26
DE4101380A1 (de)	1992-07-23

Legal Events

Date	Code	Title	Description
1994-07-09	FZDE	Discontinued

Publication	Publication Date	Title
EP1081141B1 (fr)	2005-05-04	Procédé pour la préparation de 1,2-benzisothiazol-3-ones
US3155678A (en)	1964-11-03	Certain isothiazole compounds and their production
US3822257A (en)	1974-07-02	Production of 2,1,3-benzothiadiazin-4-one-2,2-dioxides
CA2100562A1 (fr)	1992-07-19	Procede pour la production de 4h-3,1-benzoxazine-4-ones
EP1197490B1 (fr)	2004-07-21	Procédé pour la préparation du N-carboxyanhydride de la N-[1-(S)-ethoxycarbonyl-3-phénylpropyl]-L-alanine
US4673740A (en)	1987-06-16	Preparation of substituted 2-phenyl-4H-3,1-benzoxazin-4-ones
US5679827A (en)	1997-10-21	Cyanobenzenesulfenyl halide and process for preparation of 3-substituted benzisothiazole using the same
US6040443A (en)	2000-03-21	Process for the production of benzoxazinones
Fink et al.	1996	Preparation of 3-(4-pyridinylamino)-1, 2-benzisoxazoles via a nucleophilic aromatic substitution reaction
CN1095708A (zh)	1994-11-30	羟胺醚、它们的盐及其中间体的制备
JPH07215950A (ja)	1995-08-15	置換キナゾリン− ２，４− ジオンの製造方法
JPH1045706A (ja)	1998-02-17	新規ジスルフィド化合物、その製造方法および該化合物を用いるチアゼピン誘導体の製造方法
US4340742A (en)	1982-07-20	Process for making 5-mercapto-1,2,3-triazoles
JP2000169456A (ja)	2000-06-20	３−アリールジヒドロ−１，３−ベンゾオキサジン化合物の製法
GB2262097A (en)	1993-06-09	Manufacture of 4H-3,1-benzoxazin-4-ones
US4772747A (en)	1988-09-20	Preparation of 2,4,6-trichlorophenylhydrazine
IL46011A (en)	1977-10-31	Production of 3-substituted 1h-2,1,3-benzothiadiazin-4(3h)-one-2,2,-dioxides
US5710319A (en)	1998-01-20	Process for the preparation of substituted quinazoline-2,4-diones
US5288867A (en)	1994-02-22	Process for the preparation of 2-hydroxy-4,6-diaryl-1,3,5-triazines
US3655664A (en)	1972-04-11	2-aryl-4(3h)-quinazolinones
JPH01203374A (ja)	1989-08-16	ベンゾチアゼピノン誘導体の製造方法
US3317531A (en)	1967-05-02	Derivatives of pyridazonimines and a method for their preparation
IL98877A (en)	1995-05-26	Method for preparing N-alkylsulfonyl minusulfonyl ureas
Oskooie et al.	2007	Mild and efficient conversion of oximes into arylhydrazones catalysed by ferric perchlorate
US5952494A (en)	1999-09-14	Method for the preparation of pyrido benzoxazine derivatives