JPS6155501B2 - - Google Patents
Info
- Publication number
- JPS6155501B2 JPS6155501B2 JP54027211A JP2721179A JPS6155501B2 JP S6155501 B2 JPS6155501 B2 JP S6155501B2 JP 54027211 A JP54027211 A JP 54027211A JP 2721179 A JP2721179 A JP 2721179A JP S6155501 B2 JPS6155501 B2 JP S6155501B2
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- phenylthio
- benzonitrile
- added
- benzoic acid
- 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 18
- XQMIYDPLOZBCMD-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanylbenzonitrile Chemical compound C1=CC(Cl)=CC=C1SC1=CC=CC=C1C#N XQMIYDPLOZBCMD-UHFFFAOYSA-N 0.000 claims description 17
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 claims description 7
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 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 claims description 5
- -1 alkali metal salt Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 17
- NKMIZDAAUIGVMP-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1SC1=CC=C(Cl)C=C1 NKMIZDAAUIGVMP-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 7
- 239000012429 reaction media Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 6
- YNSNJGRCQCDRDM-UHFFFAOYSA-N 1-chlorothioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl YNSNJGRCQCDRDM-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- CGGXHVLRAKLYPH-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanylbenzamide Chemical compound NC(=O)C1=CC=CC=C1SC1=CC=C(Cl)C=C1 CGGXHVLRAKLYPH-UHFFFAOYSA-N 0.000 description 2
- CJNZAXGUTKBIHP-UHFFFAOYSA-N 2-iodobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 150000008359 benzonitriles Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NAQORFMUISXFRK-UHFFFAOYSA-N 1-chlorothioxanthen-9-imine Chemical compound S1C2=CC=CC=C2C(=N)C2=C1C=CC=C2Cl NAQORFMUISXFRK-UHFFFAOYSA-N 0.000 description 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 1
- JOIHPWZUQCSMJJ-UHFFFAOYSA-N 2-chloro-6-phenylsulfanylbenzonitrile Chemical compound ClC1=CC=CC(SC=2C=CC=CC=2)=C1C#N JOIHPWZUQCSMJJ-UHFFFAOYSA-N 0.000 description 1
- PWOBDMNCYMQTCE-UHFFFAOYSA-N 2-chlorobenzenethiol Chemical class SC1=CC=CC=C1Cl PWOBDMNCYMQTCE-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- XLUBZYPWTQDHNU-UHFFFAOYSA-N 2-phenylsulfanylbenzonitrile Chemical compound N#CC1=CC=CC=C1SC1=CC=CC=C1 XLUBZYPWTQDHNU-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MFZWMTSUNYWVBU-UHFFFAOYSA-N hycanthone Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(CO)=CC=C2NCCN(CC)CC MFZWMTSUNYWVBU-UHFFFAOYSA-N 0.000 description 1
- 229950000216 hycanthone Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7806741A FR2419282A1 (fr) | 1978-03-09 | 1978-03-09 | Nouveau derive de benzonitrile, son procede de preparation et son application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS554361A JPS554361A (en) | 1980-01-12 |
| JPS6155501B2 true JPS6155501B2 (en]) | 1986-11-28 |
Family
ID=9205541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2721179A Granted JPS554361A (en) | 1978-03-09 | 1979-03-07 | 22*4**chloroophenylthio**benzonitrile and its manufacture |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4264773A (en]) |
| EP (1) | EP0004257B1 (en]) |
| JP (1) | JPS554361A (en]) |
| DE (1) | DE2961851D1 (en]) |
| DK (1) | DK97079A (en]) |
| FR (1) | FR2419282A1 (en]) |
| GB (1) | GB1576802A (en]) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0285002U (en]) * | 1988-12-21 | 1990-07-03 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60114613U (ja) * | 1984-01-10 | 1985-08-02 | 株式会社スズテック | 育苗箱用自動播種装置における育苗箱取出装置 |
| CA2151074C (en) * | 1994-07-05 | 2005-08-02 | Hirokazu Kagano | Method for producing 1,2-benzisothiazol-3-ones |
| US5712401A (en) * | 1996-04-29 | 1998-01-27 | First Chemical Corporation | Processes for preparing thioxanthone and derivatives thereof |
| CN105001133B (zh) * | 2015-07-07 | 2017-04-19 | 武汉励合生物医药科技有限公司 | 一种医药中间体二芳基硫醚化合物的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB447031A (en) * | 1934-08-07 | 1935-02-13 | Cartier Sa | Improvements in or relating to lighters |
| GB447032A (en) * | 1934-08-08 | 1935-02-09 | Ig Farbenindustrie Ag | Process for the production of coloured photographic pictures |
| FR1173489A (fr) | 1957-04-04 | 1959-02-25 | Merck & Co Inc | Thiaxanthènes substitués |
| GB951651A (en) * | 1960-02-17 | 1964-03-11 | Shell Res Ltd | Substituted benzonitriles, their preparation and compositions containing them |
| US3711513A (en) * | 1970-10-05 | 1973-01-16 | Sterling Drug Inc | 1-chlorothioxanthen-9-one preparation from 2,6-dichlorobenzonitrile |
| GB1447031A (en) * | 1972-05-19 | 1976-08-25 | Wellcome Found | Tricyclic sulphones and pharmaceutical compositions containing them |
| GB1447032A (en) * | 1972-05-19 | 1976-08-25 | Wellcome Found | Tricyclic sulphones and pharmaceutical compositions containing them |
-
1978
- 1978-03-09 FR FR7806741A patent/FR2419282A1/fr active Granted
- 1978-05-12 GB GB19378/78A patent/GB1576802A/en not_active Expired
-
1979
- 1979-03-05 US US06/017,830 patent/US4264773A/en not_active Expired - Lifetime
- 1979-03-07 JP JP2721179A patent/JPS554361A/ja active Granted
- 1979-03-07 EP EP79870005A patent/EP0004257B1/fr not_active Expired
- 1979-03-07 DE DE7979870005T patent/DE2961851D1/de not_active Expired
- 1979-03-08 DK DK97079A patent/DK97079A/da not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0285002U (en]) * | 1988-12-21 | 1990-07-03 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1576802A (en) | 1980-10-15 |
| DK97079A (da) | 1979-09-10 |
| EP0004257B1 (fr) | 1982-01-20 |
| EP0004257A1 (fr) | 1979-09-19 |
| DE2961851D1 (en) | 1982-03-04 |
| FR2419282A1 (fr) | 1979-10-05 |
| JPS554361A (en) | 1980-01-12 |
| FR2419282B1 (en]) | 1980-10-03 |
| US4264773A (en) | 1981-04-28 |
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