CA1238329A - Composition a base de 5-mercapto-1,2,3-thiadiazoles; preparation - Google Patents

Composition a base de 5-mercapto-1,2,3-thiadiazoles; preparation

Info

Publication number: CA1238329A
Authority: CA; Canada
Prior art keywords: alcohol; mercapto; compound; thiadiazole; sulfide
Prior art date: 1984-10-02
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

CA000464519A

Other languages

English (en)

Inventor

Takato Nakamura

Tadakazu Sakata

Fumio Iwata

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.)

Individual

Original Assignee

Individual

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.)

1984-10-02

Filing date

1984-10-02

Publication date

1988-06-21

1984-10-02 Application filed by Individual filed Critical Individual

1984-10-02 Priority to CA000464519A priority Critical patent/CA1238329A/fr

1988-06-21 Application granted granted Critical

1988-06-21 Publication of CA1238329A publication Critical patent/CA1238329A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 60
238000004519 manufacturing process Methods 0.000 title claims abstract description 14
KZXIQMSWVSTGQX-UHFFFAOYSA-N SC1=CN=NS1 Chemical class SC1=CN=NS1 KZXIQMSWVSTGQX-UHFFFAOYSA-N 0.000 title claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 56
QFCSRTHGBBTPLC-UHFFFAOYSA-N 2h-thiadiazole-5-thione Chemical compound S=C1C=NNS1 QFCSRTHGBBTPLC-UHFFFAOYSA-N 0.000 claims abstract description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 18
150000001340 alkali metals Chemical class 0.000 claims abstract description 17
150000004820 halides Chemical class 0.000 claims abstract description 12
150000008282 halocarbons Chemical class 0.000 claims abstract description 9
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 51
238000000034 method Methods 0.000 claims description 45
238000006243 chemical reaction Methods 0.000 claims description 36
239000011541 reaction mixture Substances 0.000 claims description 32
239000000243 solution Substances 0.000 claims description 29
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 23
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 11
235000019441 ethanol Nutrition 0.000 claims description 11
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 10
239000002585 base Substances 0.000 claims description 10
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 10
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 8
238000007363 ring formation reaction Methods 0.000 claims description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
238000006482 condensation reaction Methods 0.000 claims description 7
229910052979 sodium sulfide Inorganic materials 0.000 claims description 7
229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 6
RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 claims description 6
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 5
238000005185 salting out Methods 0.000 claims description 5
150000004763 sulfides Chemical class 0.000 claims description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 claims description 4
239000008096 xylene Substances 0.000 claims description 4
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
HIVLDXAAFGCOFU-UHFFFAOYSA-N ammonium hydrosulfide Chemical compound [NH4+].[SH-] HIVLDXAAFGCOFU-UHFFFAOYSA-N 0.000 claims description 2
JGIATAMCQXIDNZ-UHFFFAOYSA-N calcium sulfide Chemical compound [Ca]=S JGIATAMCQXIDNZ-UHFFFAOYSA-N 0.000 claims description 2
YAECNLICDQSIKA-UHFFFAOYSA-L calcium;sulfanide Chemical compound [SH-].[SH-].[Ca+2] YAECNLICDQSIKA-UHFFFAOYSA-L 0.000 claims description 2
GLNWILHOFOBOFD-UHFFFAOYSA-N lithium sulfide Chemical compound [Li+].[Li+].[S-2] GLNWILHOFOBOFD-UHFFFAOYSA-N 0.000 claims description 2
QENHCSSJTJWZAL-UHFFFAOYSA-N magnesium sulfide Chemical compound [Mg+2].[S-2] QENHCSSJTJWZAL-UHFFFAOYSA-N 0.000 claims description 2
ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 claims description 2
230000001376 precipitating effect Effects 0.000 claims description 2
AHKSSQDILPRNLA-UHFFFAOYSA-N rubidium(1+);sulfide Chemical compound [S-2].[Rb+].[Rb+] AHKSSQDILPRNLA-UHFFFAOYSA-N 0.000 claims description 2
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical group [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 claims description 2
ZEGFMFQPWDMMEP-UHFFFAOYSA-N strontium;sulfide Chemical compound [S-2].[Sr+2] ZEGFMFQPWDMMEP-UHFFFAOYSA-N 0.000 claims description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 7
150000004996 alkyl benzenes Chemical class 0.000 claims 6
229960004756 ethanol Drugs 0.000 claims 4
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 3
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 3
125000003944 tolyl group Chemical group 0.000 claims 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
150000001298 alcohols Chemical class 0.000 claims 1
CJDPJFRMHVXWPT-UHFFFAOYSA-N barium sulfide Chemical compound [S-2].[Ba+2] CJDPJFRMHVXWPT-UHFFFAOYSA-N 0.000 claims 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical group [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims 1
239000003905 agrochemical Substances 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 59
239000011780 sodium chloride Substances 0.000 description 30
159000000000 sodium salts Chemical class 0.000 description 23
238000012360 testing method Methods 0.000 description 23
230000035945 sensitivity Effects 0.000 description 21
238000003756 stirring Methods 0.000 description 20
NKVBZZMINYFGSL-UHFFFAOYSA-N O.O.SC1=CN=NS1 Chemical compound O.O.SC1=CN=NS1 NKVBZZMINYFGSL-UHFFFAOYSA-N 0.000 description 17
230000015572 biosynthetic process Effects 0.000 description 16
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 16
229960002327 chloral hydrate Drugs 0.000 description 16
238000001914 filtration Methods 0.000 description 16
238000003786 synthesis reaction Methods 0.000 description 15
238000001816 cooling Methods 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
239000007795 chemical reaction product Substances 0.000 description 9
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
-1 aliphatic saturated alcohol Chemical class 0.000 description 6
239000000843 powder Substances 0.000 description 6
229940079101 sodium sulfide Drugs 0.000 description 6
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
ZGHLCBJZQLNUAZ-UHFFFAOYSA-N sodium sulfide nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2] ZGHLCBJZQLNUAZ-UHFFFAOYSA-N 0.000 description 5
229940048181 sodium sulfide nonahydrate Drugs 0.000 description 5
WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 5
238000002955 isolation Methods 0.000 description 4
239000012046 mixed solvent Substances 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
239000001103 potassium chloride Substances 0.000 description 4
235000011164 potassium chloride Nutrition 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012535 impurity Substances 0.000 description 3
229910017053 inorganic salt Inorganic materials 0.000 description 3
239000011259 mixed solution Substances 0.000 description 3
SNWLPURUNKWTPY-UHFFFAOYSA-N 2,2,2-triiodoacetaldehyde Chemical compound IC(I)(I)C=O SNWLPURUNKWTPY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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 2
FROQWJSIUIGXQA-UHFFFAOYSA-N S[S+]1N=NC=C1 Chemical class S[S+]1N=NC=C1 FROQWJSIUIGXQA-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
125000004391 aryl sulfonyl group Chemical group 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 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
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000002360 explosive Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
239000002994 raw material Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
YTGSYRVSBPFKMQ-UHFFFAOYSA-N 2,2,2-tribromoacetaldehyde Chemical compound BrC(Br)(Br)C=O YTGSYRVSBPFKMQ-UHFFFAOYSA-N 0.000 description 1
HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
HOMSOWZTBJWNHP-UHFFFAOYSA-N 5-chlorothiadiazole Chemical compound ClC1=CN=NS1 HOMSOWZTBJWNHP-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229910004874 Na2S 9H2O Inorganic materials 0.000 description 1
239000002253 acid Substances 0.000 description 1
JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
MTZQAAYXCJMINQ-UHFFFAOYSA-N azanide;rubidium(1+) Chemical compound [NH2-].[Rb+] MTZQAAYXCJMINQ-UHFFFAOYSA-N 0.000 description 1
VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
JHLCADGWXYCDQA-UHFFFAOYSA-N calcium;ethanolate Chemical compound [Ca+2].CC[O-].CC[O-] JHLCADGWXYCDQA-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
MOGRANVSCOEDEG-UHFFFAOYSA-N ethyl n-(2-chloroethylideneamino)carbamate Chemical compound CCOC(=O)NN=CCCl MOGRANVSCOEDEG-UHFFFAOYSA-N 0.000 description 1
238000004880 explosion Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000020169 heat generation Effects 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
OFGGZGXWRWYORO-UHFFFAOYSA-N methanol;tetrachloromethane Chemical compound OC.ClC(Cl)(Cl)Cl OFGGZGXWRWYORO-UHFFFAOYSA-N 0.000 description 1
229960004011 methenamine Drugs 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 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
239000007858 starting material Substances 0.000 description 1
IOTSTXWVLNQTKY-UHFFFAOYSA-N thiadiazole;dihydrate Chemical compound O.O.C1=CSN=N1 IOTSTXWVLNQTKY-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

CA000464519A 1984-10-02 1984-10-02 Composition a base de 5-mercapto-1,2,3-thiadiazoles; preparation Expired CA1238329A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000464519A CA1238329A (fr)	1984-10-02	1984-10-02	Composition a base de 5-mercapto-1,2,3-thiadiazoles; preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000464519A CA1238329A (fr)	1984-10-02	1984-10-02	Composition a base de 5-mercapto-1,2,3-thiadiazoles; preparation

Publications (1)

Publication Number	Publication Date
CA1238329A true CA1238329A (fr)	1988-06-21

Family

ID=4128819

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000464519A Expired CA1238329A (fr)	1984-10-02	1984-10-02	Composition a base de 5-mercapto-1,2,3-thiadiazoles; preparation

Country Status (1)

Country	Link
CA (1)	CA1238329A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN118995290A (zh) *	2024-08-01	2024-11-22	山西潞安太行润滑科技股份有限公司	一种润滑油用极压抗磨剂及其制备方法

1984
- 1984-10-02 CA CA000464519A patent/CA1238329A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN118995290A (zh) *	2024-08-01	2024-11-22	山西潞安太行润滑科技股份有限公司	一种润滑油用极压抗磨剂及其制备方法

Legal Events

Date	Code	Title	Description
2005-06-21	MKEX	Expiry

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CA1238329A - Composition a base de 5-mercapto-1,2,3-thiadiazoles; preparation - Google Patents

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