CH518966A - Verfahren zur Herstellung von 1,2,5-Thiadiazolderivaten - Google Patents

Verfahren zur Herstellung von 1,2,5-Thiadiazolderivaten

Info

Publication number: CH518966A
Authority: CH; Switzerland
Prior art keywords: sep; cyano; chloro; reaction; ester
Prior art date: 1969-03-19

Application number

CH248670A

Other languages

German (de)

English (en)

Inventor

Hans-Klaus Dr Vorreither

Werner Dr Obendorf

Original Assignee

Chemie Linz Ag

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.)

1969-03-19

Filing date

1970-02-20

Publication date

1972-02-15

1970-02-20 Application filed by Chemie Linz Ag filed Critical Chemie Linz Ag

1972-02-15 Publication of CH518966A publication Critical patent/CH518966A/de

Links

150000004867 thiadiazoles Chemical class 0.000 title abstract description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 14
238000006243 chemical reaction Methods 0.000 claims abstract description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
150000002148 esters Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 11
239000011593 sulfur Substances 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 6
150000004868 1,2,5-thiadiazoles Chemical class 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
239000012429 reaction media Substances 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims 1
125000005907 alkyl ester group Chemical group 0.000 abstract description 2
239000005864 Sulphur Substances 0.000 abstract 1
125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 abstract 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
239000003880 polar aprotic solvent Substances 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000005457 ice water Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 5
QLHSAELBBONESC-UHFFFAOYSA-N 3-chloro-4-ethoxy-1,2,5-thiadiazole Chemical compound CCOC1=NSN=C1Cl QLHSAELBBONESC-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000010410 layer Substances 0.000 description 2
238000001256 steam distillation Methods 0.000 description 2
FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
RYSLLBWYULVWIB-UHFFFAOYSA-N 3-chloro-4-propoxy-1,2,5-thiadiazole Chemical compound CCCOC1=NSN=C1Cl RYSLLBWYULVWIB-UHFFFAOYSA-N 0.000 description 1
239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
-1 alkyl cyanoformimidates Chemical class 0.000 description 1
125000005219 aminonitrile group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000002542 deteriorative effect Effects 0.000 description 1
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

CH248670A 1969-03-19 1970-02-20 Verfahren zur Herstellung von 1,2,5-Thiadiazolderivaten CH518966A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT267569A AT289787B (de)	1969-03-19	1969-03-19	Verfahren zur Herstellung von 1,2,5-Thiadiazolderivaten

Publications (1)

Publication Number	Publication Date
CH518966A true CH518966A (de)	1972-02-15

Family

ID=3538511

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH248670A CH518966A (de)	1969-03-19	1970-02-20	Verfahren zur Herstellung von 1,2,5-Thiadiazolderivaten

Country Status (5)

Country	Link
AT (1)	AT289787B (cs)
CH (1)	CH518966A (cs)
CS (1)	CS164265B2 (cs)
NL (1)	NL147143B (cs)
YU (1)	YU33284B (cs)

1969
- 1969-03-19 AT AT267569A patent/AT289787B/de not_active IP Right Cessation
1970
- 1970-02-20 CH CH248670A patent/CH518966A/de not_active IP Right Cessation
- 1970-03-13 NL NL7003618A patent/NL147143B/xx not_active IP Right Cessation
- 1970-03-18 YU YU68970A patent/YU33284B/xx unknown
- 1970-03-19 CS CS183770A patent/CS164265B2/cs unknown

Also Published As

Publication number	Publication date
YU33284B (en)	1976-08-31
YU68970A (en)	1976-03-31
NL7003618A (cs)	1970-09-22
NL147143B (nl)	1975-09-15
CS164265B2 (cs)	1975-11-07
AT289787B (de)	1971-05-10

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Legal Events

Date	Code	Title	Description
1988-10-31	PL	Patent ceased