UA49855C2 - Спосіб одержання 2н-1-бензопіранів - Google Patents

Спосіб одержання 2н-1-бензопіранів Download PDF

Info

Publication number: UA49855C2
Authority: UA; Ukraine
Prior art keywords: group; stage; alkyl group; differs; formula
Prior art date: 1996-08-13

Application number

UA98052383A

Other languages

English (en)

Russian (ru)

Ukrainian (uk)

Inventor

Пірре Боссард

Франсіс Фінней

Мішель Готтспонер

Original Assignee

Смітклайн Бічам Плс

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.)

1996-08-13

Filing date

1997-08-13

Publication date

2002-10-15

1997-08-13 Application filed by Смітклайн Бічам Плс filed Critical Смітклайн Бічам Плс

2002-10-15 Publication of UA49855C2 publication Critical patent/UA49855C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 29
150000000463 2H-chromenes Chemical class 0.000 title claims abstract description 6
238000004519 manufacturing process Methods 0.000 title abstract description 4
-1 nilril Chemical group 0.000 claims abstract description 34
239000003054 catalyst Substances 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
239000001257 hydrogen Substances 0.000 claims abstract description 14
150000001875 compounds Chemical class 0.000 claims abstract description 12
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
239000003960 organic solvent Substances 0.000 claims abstract description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 6
125000000217 alkyl group Chemical group 0.000 claims description 23
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
229910000027 potassium carbonate Inorganic materials 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 7
229910052814 silicon oxide Inorganic materials 0.000 claims description 6
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
239000012467 final product Substances 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
229910052901 montmorillonite Inorganic materials 0.000 claims description 3
230000009466 transformation Effects 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000003993 interaction Effects 0.000 claims description 2
239000013067 intermediate product Substances 0.000 claims description 2
125000002560 nitrile group Chemical group 0.000 claims description 2
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 abstract description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
150000002431 hydrogen Chemical group 0.000 abstract 3
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
229910052782 aluminium Chemical group 0.000 abstract 1
239000004411 aluminium Chemical group 0.000 abstract 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
239000007795 chemical reaction product Substances 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
125000004432 carbon atom Chemical group C* 0.000 description 15
SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000000047 product Substances 0.000 description 9
238000002360 preparation method Methods 0.000 description 8
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000001816 cooling Methods 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000004821 distillation Methods 0.000 description 4
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
229940073735 4-hydroxy acetophenone Drugs 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001241 acetals Chemical class 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
SFUKGEREDDIOED-UHFFFAOYSA-N 1,1-diethoxy-3-methylbut-2-ene Chemical compound CCOC(OCC)C=C(C)C SFUKGEREDDIOED-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
FAJOGLNCCHIHRH-UHFFFAOYSA-N 1,3-dioxolane;2-methylbut-2-ene Chemical compound CC=C(C)C.C1COCO1 FAJOGLNCCHIHRH-UHFFFAOYSA-N 0.000 description 1
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
PSUZFEOOWHGNNG-UHFFFAOYSA-N 1-cyano-1-(2h-pyran-2-yl)guanidine Chemical class NC(=N)N(C#N)C1OC=CC=C1 PSUZFEOOWHGNNG-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
238000004438 BET method Methods 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
238000007792 addition Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000004969 haloethyl group Chemical group 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols

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)
Saccharide Compounds (AREA)
Pyrane Compounds (AREA)
Catalysts (AREA)

UA98052383A 1996-08-13 1997-08-13 Спосіб одержання 2н-1-бензопіранів UA49855C2 (uk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH198496		1996-08-13

Publications (1)

Publication Number	Publication Date
UA49855C2 true UA49855C2 (uk)	2002-10-15

Family

ID=4223194

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA98052383A UA49855C2 (uk)	1996-08-13	1997-08-13	Спосіб одержання 2н-1-бензопіранів

Country Status (20)

Country	Link
EP (1)	EP0882035B1 (cs)
CN (1)	CN1103768C (cs)
AP (1)	AP1006A (cs)
AT (1)	ATE211739T1 (cs)
AU (1)	AU714918B2 (cs)
BG (1)	BG63570B1 (cs)
CO (1)	CO4900048A1 (cs)
CZ (1)	CZ292668B6 (cs)
DE (1)	DE69709542T2 (cs)
DK (1)	DK0882035T3 (cs)
EA (1)	EA000696B1 (cs)
ES (1)	ES2170967T3 (cs)
HU (1)	HU223351B1 (cs)
MX (1)	MX9803775A (cs)
NZ (1)	NZ330341A (cs)
PE (1)	PE107298A1 (cs)
PT (1)	PT882035E (cs)
SK (1)	SK281933B6 (cs)
UA (1)	UA49855C2 (cs)
WO (1)	WO1998006713A1 (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005014586A1 (en) *	2003-08-08	2005-02-17	Arpida Ag	Novel process for the preparation of 2h-chromenes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW310327B (cs) *	1993-06-18	1997-07-11	Bristol Myers Squibb Co

1997
- 1997-08-13 AT AT97944779T patent/ATE211739T1/de active
- 1997-08-13 EA EA199800370A patent/EA000696B1/ru not_active IP Right Cessation
- 1997-08-13 DK DK97944779T patent/DK0882035T3/da active
- 1997-08-13 HU HU9902584A patent/HU223351B1/hu active IP Right Grant
- 1997-08-13 DE DE69709542T patent/DE69709542T2/de not_active Expired - Lifetime
- 1997-08-13 CZ CZ19981469A patent/CZ292668B6/cs not_active IP Right Cessation
- 1997-08-13 AU AU46179/97A patent/AU714918B2/en not_active Expired
- 1997-08-13 ES ES97944779T patent/ES2170967T3/es not_active Expired - Lifetime
- 1997-08-13 PT PT97944779T patent/PT882035E/pt unknown
- 1997-08-13 AP APAP/P/1998/001232A patent/AP1006A/en active
- 1997-08-13 CN CN97191398A patent/CN1103768C/zh not_active Expired - Lifetime
- 1997-08-13 SK SK612-98A patent/SK281933B6/sk not_active IP Right Cessation
- 1997-08-13 EP EP97944779A patent/EP0882035B1/en not_active Expired - Lifetime
- 1997-08-13 UA UA98052383A patent/UA49855C2/uk unknown
- 1997-08-13 NZ NZ330341A patent/NZ330341A/en not_active IP Right Cessation
- 1997-08-13 WO PCT/EP1997/004569 patent/WO1998006713A1/en not_active Ceased
- 1997-08-20 PE PE1997000737A patent/PE107298A1/es not_active IP Right Cessation
- 1997-08-22 CO CO97048490A patent/CO4900048A1/es unknown
1998
- 1998-05-12 MX MX9803775A patent/MX9803775A/es active IP Right Grant
- 1998-05-12 BG BG102442A patent/BG63570B1/bg unknown

Also Published As

Publication number	Publication date
EA199800370A1 (ru)	1998-10-29
DK0882035T3 (da)	2002-04-29
CN1205007A (zh)	1999-01-13
PT882035E (pt)	2002-06-28
AU714918B2 (en)	2000-01-13
AU4617997A (en)	1998-03-06
HK1020438A1 (en)	2000-04-20
CZ146998A3 (cs)	1998-10-14
CO4900048A1 (es)	2000-03-27
HUP9902584A3 (en)	2001-06-28
ES2170967T3 (es)	2002-08-16
SK61298A3 (en)	1998-12-02
DE69709542D1 (de)	2002-02-14
WO1998006713A1 (en)	1998-02-19
ATE211739T1 (de)	2002-01-15
HU223351B1 (hu)	2004-06-28
EP0882035A1 (en)	1998-12-09
CN1103768C (zh)	2003-03-26
HUP9902584A2 (hu)	2001-05-28
AP9801232A0 (en)	1998-06-30
PE107298A1 (es)	1999-03-20
NZ330341A (en)	2000-02-28
EP0882035B1 (en)	2002-01-09
CZ292668B6 (cs)	2003-11-12
EA000696B1 (ru)	2000-02-28
DE69709542T2 (de)	2002-08-22
BG102442A (en)	1999-04-30
SK281933B6 (sk)	2001-09-11
MX9803775A (es)	1998-09-30
AP1006A (en)	2001-08-29
BG63570B1 (bg)	2002-05-31

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