JPH0460992B2 - - Google Patents
Info
- Publication number
- JPH0460992B2 JPH0460992B2 JP12011783A JP12011783A JPH0460992B2 JP H0460992 B2 JPH0460992 B2 JP H0460992B2 JP 12011783 A JP12011783 A JP 12011783A JP 12011783 A JP12011783 A JP 12011783A JP H0460992 B2 JPH0460992 B2 JP H0460992B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- water
- acetone
- copper
- benzothiazolyl
- Prior art date
- 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
Links
- 238000004519 manufacturing process Methods 0.000 claims description 7
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 claims description 7
- 229910001385 heavy metal Inorganic materials 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- -1 alkali metal salt Chemical class 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- JHCPRMVDOCTAMG-UHFFFAOYSA-L copper;benzenesulfinate Chemical compound [Cu+2].[O-]S(=O)C1=CC=CC=C1.[O-]S(=O)C1=CC=CC=C1 JHCPRMVDOCTAMG-UHFFFAOYSA-L 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- SJIHLYOMBYTQHT-UHFFFAOYSA-N [2-(1,3-benzothiazol-2-yl)phenyl]-hydroxy-oxo-sulfanylidene-lambda6-sulfane Chemical compound C1=CC=C(C(=C1)C2=NC3=CC=CC=C3S2)S(=O)(=S)O SJIHLYOMBYTQHT-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- HOHVUEGHUQRFNQ-UHFFFAOYSA-N 1,3-benzothiazol-2-yloxy-oxo-phenyl-sulfanylidene-$l^{6}-sulfane Chemical compound N=1C2=CC=CC=C2SC=1OS(=S)(=O)C1=CC=CC=C1 HOHVUEGHUQRFNQ-UHFFFAOYSA-N 0.000 description 2
- RWYJGJWCMWVUAB-UHFFFAOYSA-N CC1=CC=CC2=C1N=C(C(C=CC=C1)=C1S(O)(=O)=S)S2 Chemical compound CC1=CC=CC2=C1N=C(C(C=CC=C1)=C1S(O)(=O)=S)S2 RWYJGJWCMWVUAB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- GOSLZYRGUTVYOP-UHFFFAOYSA-N (5-methoxy-1,3-benzothiazol-2-yl)oxy-oxo-phenyl-sulfanylidene-$l^{6}-sulfane Chemical compound N=1C2=CC(OC)=CC=C2SC=1OS(=O)(=S)C1=CC=CC=C1 GOSLZYRGUTVYOP-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- NEQIINRMDYNPTO-UHFFFAOYSA-N 1,3-benzothiazol-2-yloxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OC1=NC2=CC=CC=C2S1 NEQIINRMDYNPTO-UHFFFAOYSA-N 0.000 description 1
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- SSQNKTBATJCFLF-UHFFFAOYSA-N 4-methyl-2-[(4-methyl-1,3-benzothiazol-2-yl)disulfanyl]-1,3-benzothiazole Chemical compound C1=CC=C2SC(SSC=3SC=4C=CC=C(C=4N=3)C)=NC2=C1C SSQNKTBATJCFLF-UHFFFAOYSA-N 0.000 description 1
- SRJKHNTVCHLOIA-UHFFFAOYSA-N 5-chloro-2-[(5-chloro-1,3-benzothiazol-2-yl)disulfanyl]-1,3-benzothiazole Chemical compound ClC1=CC=C2SC(SSC=3SC4=CC=C(C=C4N=3)Cl)=NC2=C1 SRJKHNTVCHLOIA-UHFFFAOYSA-N 0.000 description 1
- QSOHSUYZXBNXBQ-UHFFFAOYSA-N 5-methoxy-2-[(5-methoxy-1,3-benzothiazol-2-yl)disulfanyl]-1,3-benzothiazole Chemical compound COC1=CC=C2SC(SSC=3SC4=CC=C(C=C4N=3)OC)=NC2=C1 QSOHSUYZXBNXBQ-UHFFFAOYSA-N 0.000 description 1
- SKQWJYKBNFADLR-UHFFFAOYSA-N 6-methyl-2-[(6-methyl-1,3-benzothiazol-2-yl)disulfanyl]-1,3-benzothiazole Chemical compound C1=C(C)C=C2SC(SSC3=NC4=CC=C(C=C4S3)C)=NC2=C1 SKQWJYKBNFADLR-UHFFFAOYSA-N 0.000 description 1
- MFCGAIPEIISLHT-UHFFFAOYSA-N 6-nitro-2-[(6-nitro-1,3-benzothiazol-2-yl)disulfanyl]-1,3-benzothiazole Chemical compound C1=C([N+]([O-])=O)C=C2SC(SSC3=NC4=CC=C(C=C4S3)[N+](=O)[O-])=NC2=C1 MFCGAIPEIISLHT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical class [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- GHJRPPPCGWIZJZ-UHFFFAOYSA-N hydroxy-[2-(6-nitro-1,3-benzothiazol-2-yl)phenyl]-oxo-sulfanylidene-lambda6-sulfane Chemical compound C1=CC=C(C(=C1)C2=NC3=C(S2)C=C(C=C3)[N+](=O)[O-])S(=O)(=S)O GHJRPPPCGWIZJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CPXGFFUFUXXZGC-UHFFFAOYSA-M silver;4-methylbenzenesulfinate Chemical compound [Ag+].CC1=CC=C(S([O-])=O)C=C1 CPXGFFUFUXXZGC-UHFFFAOYSA-M 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12011783A JPS6011480A (ja) | 1983-06-30 | 1983-06-30 | チオスルホネ−トの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12011783A JPS6011480A (ja) | 1983-06-30 | 1983-06-30 | チオスルホネ−トの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6011480A JPS6011480A (ja) | 1985-01-21 |
| JPH0460992B2 true JPH0460992B2 (ko) | 1992-09-29 |
Family
ID=14778372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12011783A Granted JPS6011480A (ja) | 1983-06-30 | 1983-06-30 | チオスルホネ−トの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6011480A (ko) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USD868704S1 (en) | 2017-11-15 | 2019-12-03 | Corning Research & Development Corporation | Cap for optical fiber connectors |
| USD868703S1 (en) | 2017-11-15 | 2019-12-03 | Corning Research & Development Corporation | Cap for optical fiber connectors |
| USD879725S1 (en) | 2017-10-31 | 2020-03-31 | Corning Research & Development Corporation | Cap for optical fiber connectors |
| USD883231S1 (en) | 2017-10-31 | 2020-05-05 | Corning Research & Development Corporation | Cap for optical fiber connectors |
| USD942955S1 (en) | 2019-12-19 | 2022-02-08 | Corning Research & Development Corporation | Cap for an adapter |
-
1983
- 1983-06-30 JP JP12011783A patent/JPS6011480A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USD879725S1 (en) | 2017-10-31 | 2020-03-31 | Corning Research & Development Corporation | Cap for optical fiber connectors |
| USD883231S1 (en) | 2017-10-31 | 2020-05-05 | Corning Research & Development Corporation | Cap for optical fiber connectors |
| USD868704S1 (en) | 2017-11-15 | 2019-12-03 | Corning Research & Development Corporation | Cap for optical fiber connectors |
| USD868703S1 (en) | 2017-11-15 | 2019-12-03 | Corning Research & Development Corporation | Cap for optical fiber connectors |
| USD942955S1 (en) | 2019-12-19 | 2022-02-08 | Corning Research & Development Corporation | Cap for an adapter |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6011480A (ja) | 1985-01-21 |
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