CA1104145A - Process for the manufacture of butenolide derivatives - Google Patents

Process for the manufacture of butenolide derivatives

Info

Publication number: CA1104145A
Authority: CA; Canada
Prior art keywords: formula; compound; single bond; prepared; methyl
Prior art date: 1976-09-13
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.): Expired

Application number

CA286,399A

Other languages

English (en)

French (fr)

Inventor

Alan W. Johnson

Ahmed Hassanali-Walji

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.)

INTERNATIONAL DEVELOPMENT RESEARCH CENTRE

Original Assignee

INTERNATIONAL DEVELOPMENT RESEARCH CENTRE

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.)

1976-09-13

Filing date

1977-09-09

Publication date

1981-06-30

1977-09-09 Application filed by INTERNATIONAL DEVELOPMENT RESEARCH CENTRE filed Critical INTERNATIONAL DEVELOPMENT RESEARCH CENTRE

1981-06-30 Application granted granted Critical

1981-06-30 Publication of CA1104145A publication Critical patent/CA1104145A/en

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 5
238000000034 method Methods 0.000 title claims description 33
SQEBMLCQNJOCBG-HVHJFMEUSA-N (5s)-3-(hydroxymethyl)-5-methoxy-4-methyl-5-[(e)-2-phenylethenyl]furan-2-one Chemical class C=1C=CC=CC=1/C=C/[C@]1(OC)OC(=O)C(CO)=C1C SQEBMLCQNJOCBG-HVHJFMEUSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 32
-1 alkali metal salt Chemical class 0.000 claims abstract description 6
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
159000000000 sodium salts Chemical class 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 5
239000000376 reactant Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
125000003700 epoxy group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 claims 2
238000001311 chemical methods and process Methods 0.000 abstract description 2
GCVGDGFZLSSUIO-UHFFFAOYSA-N 4-chloro-2h-furan-5-one Chemical compound ClC1=CCOC1=O GCVGDGFZLSSUIO-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
RZQNZDURDLIZRR-UHFFFAOYSA-N 4-chloro-3-methyl-2h-furan-5-one Chemical compound CC1=C(Cl)C(=O)OC1 RZQNZDURDLIZRR-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
YNBMDVQFFDOHBI-UHFFFAOYSA-N C(=O)CC(=O)O.OC1CC2C(C1)O2 Chemical compound C(=O)CC(=O)O.OC1CC2C(C1)O2 YNBMDVQFFDOHBI-UHFFFAOYSA-N 0.000 description 1
241000263342 Orobanche crenata Species 0.000 description 1
241000404576 Phelipanche aegyptiaca Species 0.000 description 1
241000201310 Phelipanche ramosa Species 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
240000001705 Striga asiatica Species 0.000 description 1
241000960395 Striga hermonthica Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA286,399A 1976-09-13 1977-09-09 Process for the manufacture of butenolide derivatives Expired CA1104145A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB37760/76		1976-09-13
GB3776076		1976-09-13

Publications (1)

Publication Number	Publication Date
CA1104145A true CA1104145A (en)	1981-06-30

Family

ID=10398816

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA286,399A Expired CA1104145A (en)	1976-09-13	1977-09-09	Process for the manufacture of butenolide derivatives

Country Status (9)

Country	Link
JP (1)	JPS5334769A (de)
BE (1)	BE858646A (de)
CA (1)	CA1104145A (de)
CH (1)	CH628631A5 (de)
DE (1)	DE2740801A1 (de)
DK (1)	DK406777A (de)
FR (1)	FR2364212A1 (de)
NL (1)	NL7709873A (de)
SE (1)	SE7710205L (de)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1470097A (en) *	1974-04-18	1977-04-14	Int Dev Res Centre	Alpha-butyrolactone derivatives as germination factors

1977
- 1977-09-08 NL NL7709873A patent/NL7709873A/xx not_active Application Discontinuation
- 1977-09-09 DE DE19772740801 patent/DE2740801A1/de not_active Withdrawn
- 1977-09-09 FR FR7727398A patent/FR2364212A1/fr not_active Withdrawn
- 1977-09-09 CA CA286,399A patent/CA1104145A/en not_active Expired
- 1977-09-12 SE SE7710205A patent/SE7710205L/xx unknown
- 1977-09-13 DK DK406777A patent/DK406777A/da not_active Application Discontinuation
- 1977-09-13 JP JP10955677A patent/JPS5334769A/ja active Pending
- 1977-09-13 CH CH1115677A patent/CH628631A5/de not_active IP Right Cessation
- 1977-09-13 BE BE180863A patent/BE858646A/xx unknown

Also Published As

Publication number	Publication date
NL7709873A (nl)	1978-03-15
JPS5334769A (en)	1978-03-31
DK406777A (da)	1978-03-14
DE2740801A1 (de)	1978-03-16
BE858646A (fr)	1978-03-13
CH628631A5 (en)	1982-03-15
FR2364212A1 (fr)	1978-04-07
SE7710205L (sv)	1978-03-14

Legal Events

Date	Code	Title	Description
1998-06-30	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 19980630

Publication	Publication Date	Title
SU721000A1 (ru)	1986-11-30	Способ получени ациланилинов
SU489306A3 (ru)	1975-10-25	Способ получени простагландиновых эфиров
Kulka	1956	Hydrolysis and hydrazinolysis of esters of n, n-dimethyldithiocarbamic acid: a method for the preparation of mercaptans
CA1104145A (en)	1981-06-30	Process for the manufacture of butenolide derivatives
US3544584A (en)	1970-12-01	Certain 5-alkyl-3-hydroxyisoxazoles
CA1329618C (en)	1994-05-17	Aminoalkyl-substituted heterocyclic sulfur compounds
US3636037A (en)	1972-01-18	Carbonic esters of 4-nitrophenol
US4394516A (en)	1983-07-19	Process for the preparation of a furan derivative
US4054576A (en)	1977-10-18	Insect repellant compounds
US3998999A (en)	1976-12-21	Process for preparing pyrazomycin and pyrazomycin B
SU725542A1 (ru)	1980-03-30	Фунгицидное средство
KR970011285B1 (ko)	1997-07-09	3,3-디아릴아크릴 산 아미드의 제법
US4101670A (en)	1978-07-18	Germicidal and acaricidal compositions
EP0004107A1 (de)	1979-09-19	3-Azabicyclo(3.1.0)Hexan-Derivate, Verfahren zu ihrer Herstellung, diese enthaltende biologisch aktive Zusammensetzungen und ein Verfahren zu ihrer Anwendung als Herbizide
US3915962A (en)	1975-10-28	Procedure for the preparation of aromatic 2-imino-1,3-dithietanes
US2799686A (en)	1957-07-16	Alpha-bromo-beta (5-nitro-2-thienyl)-acrolein
SU472506A3 (ru)	1975-05-30	Способ получени производных морфолина
JPS5936994B2 (ja)	1984-09-06	Ｎ−スルフイニルカルバメ−ト
US4028411A (en)	1977-06-07	Insect repellent dimethylbenzamides
US4382954A (en)	1983-05-10	Fungicidal N-1-substituted cyclopropyl-N-acyl-2,6-dialkylaniline
US4036960A (en)	1977-07-19	1,3-Benzoxazin-4-one derivatives and their use as ovicides
SU622398A3 (ru)	1978-08-30	Способ получени производных оксима или их солей
KR0145401B1 (ko)	1998-07-15	실릴아크릴레이트 유도체 및 그 제조방법
JPH01168664A (ja)	1989-07-04	シクロヘキセノン誘導体およびその製造法
US4039316A (en)	1977-08-02	3-Methoxy crotonanilides as herbicides