DD202708A5 - Verfahren zur herstellung von 5,6-dihydro-2-methyl-n-phenyl-1,4-oxathin-3-karboxamid - Google Patents

Verfahren zur herstellung von 5,6-dihydro-2-methyl-n-phenyl-1,4-oxathin-3-karboxamid Download PDF

Info

Publication number: DD202708A5
Authority: DD; German Democratic Republic
Prior art keywords: hydroxyethyl; item; reaction; mercaptoethanol; reaction mixture
Prior art date: 1981-08-11

Application number

DD82242363A

Other languages

German (de)

English (en)

Inventor

George Liebermann

Frederick M M Hager

Original Assignee

Uniroyal 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.)

1981-08-11

Filing date

1982-08-09

Publication date

1983-09-28

1982-08-09 Application filed by Uniroyal Ltd filed Critical Uniroyal Ltd

1983-09-28 Publication of DD202708A5 publication Critical patent/DD202708A5/de

Links

238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 37
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims abstract description 21
KYNFOMQIXZUKRK-UHFFFAOYSA-N 2,2'-dithiodiethanol Chemical compound OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims abstract description 8
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 52
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 38
238000006243 chemical reaction Methods 0.000 claims description 22
239000011541 reaction mixture Substances 0.000 claims description 21
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 15
230000003647 oxidation Effects 0.000 claims description 10
238000007254 oxidation reaction Methods 0.000 claims description 10
238000007363 ring formation reaction Methods 0.000 claims description 10
238000011065 in-situ storage Methods 0.000 claims description 7
JZOFKEVYAHEKJC-UHFFFAOYSA-N N-phenyl-2,5-diazabicyclo[2.2.0]hexa-1(4),2,5-triene-3-carboxamide Chemical compound N1=C(C2=C1C=N2)C(=O)NC1=CC=CC=C1 JZOFKEVYAHEKJC-UHFFFAOYSA-N 0.000 claims description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
239000000047 product Substances 0.000 claims description 5
230000001476 alcoholic effect Effects 0.000 claims description 4
-1 (2-hydroxyethyl) thio Chemical group 0.000 claims description 3
239000003518 caustics Substances 0.000 claims description 3
239000008346 aqueous phase Substances 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
239000006227 byproduct Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000003513 alkali Substances 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
230000000855 fungicidal effect Effects 0.000 abstract description 3
GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 abstract description 2
239000000417 fungicide Substances 0.000 abstract description 2
CSQOAEIMKOPVBK-UHFFFAOYSA-N 2-(2-hydroxyethylsulfanyl)-3-oxo-n-phenylbutanamide Chemical compound OCCSC(C(=O)C)C(=O)NC1=CC=CC=C1 CSQOAEIMKOPVBK-UHFFFAOYSA-N 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 11
238000007792 addition Methods 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000005991 sulfenylation reaction Methods 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
YBKGERLDRMINOV-UHFFFAOYSA-N oxathiine Chemical compound O1SC=CC=C1 YBKGERLDRMINOV-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
229930194542 Keto Natural products 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002085 enols Chemical group 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
239000010410 layer Substances 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
CPRVXMQHLPTWLY-UHFFFAOYSA-N 1,4-oxathiine Chemical compound O1C=CSC=C1 CPRVXMQHLPTWLY-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 1
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
229910000361 cobalt sulfate Inorganic materials 0.000 description 1
229940044175 cobalt sulfate Drugs 0.000 description 1
KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000017525 heat dissipation Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
MUULCPJUUOCRAT-UHFFFAOYSA-N n-(2-hydroxypropyl)butanamide Chemical compound CCCC(=O)NCC(C)O MUULCPJUUOCRAT-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000005694 sulfonylation reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
238000004448 titration Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD82242363A 1981-08-11 1982-08-09 Verfahren zur herstellung von 5,6-dihydro-2-methyl-n-phenyl-1,4-oxathin-3-karboxamid DD202708A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000383592A CA1166262A (fr)	1981-08-11	1981-08-11	Synthese d'intermediaires menant a la production industrielle de 5,6-dihydro-2-methyl-n-phenyl-1,4- oxathiin-3-carboxamide

Publications (1)

Publication Number	Publication Date
DD202708A5 true DD202708A5 (de)	1983-09-28

Family

ID=4120659

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD82242363A DD202708A5 (de)	1981-08-11	1982-08-09	Verfahren zur herstellung von 5,6-dihydro-2-methyl-n-phenyl-1,4-oxathin-3-karboxamid

Country Status (22)

Country	Link
US (1)	US4359579A (fr)
EP (1)	EP0072106B1 (fr)
JP (1)	JPS6052153B2 (fr)
KR (1)	KR860000102B1 (fr)
AU (1)	AU550553B2 (fr)
BG (1)	BG37076A3 (fr)
BR (1)	BR8204245A (fr)
CA (1)	CA1166262A (fr)
DD (1)	DD202708A5 (fr)
DE (1)	DE3266930D1 (fr)
ES (1)	ES8400424A1 (fr)
GB (1)	GB2103606B (fr)
GR (1)	GR77221B (fr)
HU (1)	HU187781B (fr)
IL (1)	IL66369A0 (fr)
PL (1)	PL237854A1 (fr)
RO (1)	RO85553B1 (fr)
SU (1)	SU1155156A3 (fr)
TR (1)	TR21590A (fr)
YU (1)	YU173682A (fr)
ZA (1)	ZA824846B (fr)
ZW (1)	ZW14082A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5268389A (en)	1989-10-16	1993-12-07	Uniroyal Chemical Company, Inc.	Thiocarboxylate ester compounds compositions containing the same

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3393202A (en) *	1965-04-26	1968-07-16	Uniroyal Inc	2, 3-dihydro-5-carboxamido-6-methyl-1, 4-oxathins and method of making same
US3399214A (en) *	1965-11-05	1968-08-27	Uniroyal Inc	Oxides of carboxamido oxathiins
US3728357A (en) *	1970-09-08	1973-04-17	Uniroyal Inc	2-(substituted-methyl)-5,6-dihydro-1,4-oxathiin-3-carboxamides
DE2164805A1 (de) *	1970-12-29	1972-07-13	Fuji Photo Film Co. Ltd., Ashigara-Kamigun, Kanagawa (Japan)	Verfahren zur Herstellung einer eine Thiogruppe enthaltenden Verbindung
CA1036167A (fr) *	1977-05-06	1978-08-08	Wha S. Lee	Procede de preparation de derives de dihydro-5,6 methyl-2 oxathiine-1,4
US4230871A (en) *	1979-04-02	1980-10-28	Lee Wha S	Process for preparing 5,6-dihydro-2-methyl-1,4-oxathiin derivatives

1981
- 1981-08-11 CA CA000383592A patent/CA1166262A/fr not_active Expired
- 1981-08-24 US US06/295,394 patent/US4359579A/en not_active Expired - Lifetime
1982
- 1982-07-06 AU AU85629/82A patent/AU550553B2/en not_active Ceased
- 1982-07-07 ZA ZA824846A patent/ZA824846B/xx unknown
- 1982-07-12 EP EP82303650A patent/EP0072106B1/fr not_active Expired
- 1982-07-12 DE DE8282303650T patent/DE3266930D1/de not_active Expired
- 1982-07-12 GB GB08220156A patent/GB2103606B/en not_active Expired
- 1982-07-13 ZW ZW140/82A patent/ZW14082A1/xx unknown
- 1982-07-21 BR BR8204245A patent/BR8204245A/pt unknown
- 1982-07-21 IL IL66369A patent/IL66369A0/xx not_active IP Right Cessation
- 1982-08-05 TR TR21590A patent/TR21590A/xx unknown
- 1982-08-09 RO RO108416A patent/RO85553B1/ro unknown
- 1982-08-09 BG BG057688A patent/BG37076A3/xx unknown
- 1982-08-09 GR GR68985A patent/GR77221B/el unknown
- 1982-08-09 DD DD82242363A patent/DD202708A5/de unknown
- 1982-08-10 PL PL23785482A patent/PL237854A1/xx unknown
- 1982-08-10 JP JP57139099A patent/JPS6052153B2/ja not_active Expired
- 1982-08-10 ES ES514886A patent/ES8400424A1/es not_active Expired
- 1982-08-10 SU SU823476700A patent/SU1155156A3/ru active
- 1982-08-10 HU HU822582A patent/HU187781B/hu unknown
- 1982-08-10 KR KR8203584A patent/KR860000102B1/ko not_active Expired
- 1982-08-10 YU YU01736/82A patent/YU173682A/xx unknown

Also Published As

Publication number	Publication date
GR77221B (fr)	1984-09-11
ZW14082A1 (en)	1982-10-06
DE3266930D1 (en)	1985-11-21
RO85553A2 (fr)	1985-02-25
AU8562982A (en)	1983-02-17
PL237854A1 (en)	1983-04-11
JPS6052153B2 (ja)	1985-11-18
BR8204245A (pt)	1983-07-12
RO85553B1 (ro)	1985-02-28
TR21590A (tr)	1984-11-12
EP0072106B1 (fr)	1985-10-16
BG37076A3 (en)	1985-03-15
CA1166262A (fr)	1984-04-24
ES514886A0 (es)	1983-11-01
KR860000102B1 (ko)	1986-02-19
KR840001153A (ko)	1984-03-28
YU173682A (en)	1984-12-31
HU187781B (en)	1986-02-28
SU1155156A3 (ru)	1985-05-07
ZA824846B (en)	1983-04-27
EP0072106A1 (fr)	1983-02-16
IL66369A0 (en)	1982-11-30
JPS5838280A (ja)	1983-03-05
GB2103606B (en)	1985-09-18
US4359579A (en)	1982-11-16
AU550553B2 (en)	1986-03-27
ES8400424A1 (es)	1983-11-01
GB2103606A (en)	1983-02-23

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