CA1228073A - Methode de synthese du 5-thio-1,2,3-thiadiazole - Google Patents

Methode de synthese du 5-thio-1,2,3-thiadiazole

Info

Publication number: CA1228073A
Authority: CA; Canada
Prior art keywords: methyl; sodium; solution; hours; propanoate
Prior art date: 1982-09-27
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

CA000524600A

Other languages

English (en)

Inventor

William V. Curran

Martin L. Sassiver

James H. Boothe

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.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

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.)

1982-09-27

Filing date

1986-12-04

Publication date

1987-10-13

1982-09-27 Priority claimed from US06/424,825 external-priority patent/US4454336A/en

1986-12-04 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1986-12-04 Priority to CA000524600A priority Critical patent/CA1228073A/fr

1987-10-13 Application granted granted Critical

1987-10-13 Publication of CA1228073A publication Critical patent/CA1228073A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 12
230000015572 biosynthetic process Effects 0.000 title abstract 2
238000003786 synthesis reaction Methods 0.000 title abstract 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
-1 p-toluenesulfonyl Chemical group 0.000 claims description 8
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 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
239000011734 sodium Substances 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 4
239000001257 hydrogen Substances 0.000 claims 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
KZXIQMSWVSTGQX-UHFFFAOYSA-N SC1=CN=NS1 Chemical class SC1=CN=NS1 KZXIQMSWVSTGQX-UHFFFAOYSA-N 0.000 abstract description 2
239000003242 anti bacterial agent Substances 0.000 abstract description 2
238000002360 preparation method Methods 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 10
239000003921 oil Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
150000007857 hydrazones Chemical class 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
NGWIFDMMRFVKGE-UHFFFAOYSA-N methyl 3-(2-oxoethylsulfanyl)propanoate Chemical compound COC(=O)CCSCC=O NGWIFDMMRFVKGE-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 2
UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
XKYWPGDHAXBPMI-UHFFFAOYSA-N NC(=O)NN=C(OC)CCSCC=O Chemical compound NC(=O)NN=C(OC)CCSCC=O XKYWPGDHAXBPMI-UHFFFAOYSA-N 0.000 description 2
MKYAOTISEBUZEU-UHFFFAOYSA-N O=CCSCCC(OC)=NNS(=O)(=O)C1=CC=C(C)C=C1 Chemical compound O=CCSCCC(OC)=NNS(=O)(=O)C1=CC=C(C)C=C1 MKYAOTISEBUZEU-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
239000012267 brine Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000012043 crude product Substances 0.000 description 2
VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
150000002429 hydrazines Chemical class 0.000 description 2
IRWDBTCPLYWNNZ-UHFFFAOYSA-N methyl 3-(thiadiazol-5-ylsulfanyl)propanoate Chemical compound COC(=O)CCSC1=CN=NS1 IRWDBTCPLYWNNZ-UHFFFAOYSA-N 0.000 description 2
RVEBJDGWKWKYBH-UHFFFAOYSA-N o-methyl propanethioate Chemical compound CCC(=S)OC RVEBJDGWKWKYBH-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
150000007659 semicarbazones Chemical class 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical class C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
229910052700 potassium Chemical group 0.000 description 1
239000011591 potassium Chemical group 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229940087562 sodium acetate trihydrate Drugs 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HVUPQFWBIIOQQE-UHFFFAOYSA-M sodium;thiadiazole-5-thiolate Chemical compound [Na+].[S-]C1=CN=NS1 HVUPQFWBIIOQQE-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
239000011800 void material Substances 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)

CA000524600A 1982-09-27 1986-12-04 Methode de synthese du 5-thio-1,2,3-thiadiazole Expired CA1228073A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000524600A CA1228073A (fr)	1982-09-27	1986-12-04	Methode de synthese du 5-thio-1,2,3-thiadiazole

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/424,825 US4454336A (en)	1982-09-27	1982-09-27	Derivatives of 3-(formylmethylthio)-propanoate
US424,825		1982-09-27
CA000437550A CA1229619A (fr)	1982-09-27	1983-09-26	Synthese de 5-thio-1,2,3-thiadiazole
CA000524600A CA1228073A (fr)	1982-09-27	1986-12-04	Methode de synthese du 5-thio-1,2,3-thiadiazole

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000437550A Division CA1229619A (fr)	1982-09-27	1983-09-26	Synthese de 5-thio-1,2,3-thiadiazole

Publications (1)

Publication Number	Publication Date
CA1228073A true CA1228073A (fr)	1987-10-13

Family

ID=25670162

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000524600A Expired CA1228073A (fr)	1982-09-27	1986-12-04	Methode de synthese du 5-thio-1,2,3-thiadiazole

Country Status (1)

Country	Link
CA (1)	CA1228073A (fr)

1986
- 1986-12-04 CA CA000524600A patent/CA1228073A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2004-10-13	MKEX	Expiry

Publication	Publication Date	Title
JPS6251955B2 (fr)	1987-11-02
US4196292A (en)	1980-04-01	6-Substituted amiloride derivatives
CH616161A5 (fr)	1980-03-14
EP0045910B1 (fr)	1984-10-10	Dérivés de l'indol et leur procédé de préparation
KR920002295B1 (ko)	1992-03-21	프롤리디논 유도체의 제조방법
CA1228073A (fr)	1987-10-13	Methode de synthese du 5-thio-1,2,3-thiadiazole
US4454336A (en)	1984-06-12	Derivatives of 3-(formylmethylthio)-propanoate
US4751293A (en)	1988-06-14	Process for preparation of N6 -substituted 3',5'-cyclic adenosine monophosphate and salt thereof
BE897952A (fr)	1984-01-30	Procede de production d'imidazoles et intermediaires utilises a cet effet
EP0073704B1 (fr)	1986-11-12	Nouveaux nitriles hétérocycliques, leur préparation et leur utilisation pour la préparation de médicaments
FR2511681A1 (fr)	1983-02-25	Procede pour la preparation de derives de 3-exo-methylenecephame
CA2128560A1 (fr)	1995-01-24	Piperazines substituees, leur procede de preparation et les compositions pharmaceutiques les contenant
JPH0662591B2 (ja)	1994-08-17	新規なチオプロリン誘導体
US5907036A (en)	1999-05-25	Procedures for obtaining ribo-C-nucleosides
EP0713865B1 (fr)	1999-02-10	Dérivés d'acide 2-aminobenzènesulfonique et de chlorure de 2-aminobenzènesulfonyle, leur préparation et leur utilisation comme intermédiaires de synthèse
JPH038349B2 (fr)	1991-02-05
FR2482595A1 (fr)	1981-11-20	Procede de preparation de n-(2-(((5-(dial-kylamino) - methyl-2-furanyl)-methyl)-thio)-ethyl)-n'-alkyl-2-nitro-1,1-ethenediamines et des intermediaires de synthese mis en oeuvre dans ce procede
US4482723A (en)	1984-11-13	Process for preparation of 4-acetyl-2-substituted-imidazoles
US5457206A (en)	1995-10-10	Process for preparing intermediates to nizatidine and related compounds
JPS5910351B2 (ja)	1984-03-08	３−オキシ−１，２，４−トリアゾ−ル誘導体の製造方法
JPH0256354B2 (fr)	1990-11-29
JP4004082B2 (ja)	2007-11-07	環状ニトログアニジン誘導体の製造法
EP0599732B1 (fr)	1997-03-12	Dérivés de 1-phénylbicyclo[2.2.2]octane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
KR820001991B1 (ko)	1982-10-23	퓨란 유도체의 제조방법
JP3003187B2 (ja)	2000-01-24	含窒素ヘテロ環の製造法