JP5795519B2 - クロロスルホニルベンゾイルクロライド化合物の製造方法 - Google Patents
クロロスルホニルベンゾイルクロライド化合物の製造方法 Download PDFInfo
- Publication number
- JP5795519B2 JP5795519B2 JP2011240058A JP2011240058A JP5795519B2 JP 5795519 B2 JP5795519 B2 JP 5795519B2 JP 2011240058 A JP2011240058 A JP 2011240058A JP 2011240058 A JP2011240058 A JP 2011240058A JP 5795519 B2 JP5795519 B2 JP 5795519B2
- Authority
- JP
- Japan
- Prior art keywords
- chloride
- chlorosulfonylbenzoyl
- formula
- chloride compound
- group
- 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 - Fee Related
Links
- FQVVJFIHGLIEBJ-UHFFFAOYSA-N 2-chlorosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1S(Cl)(=O)=O FQVVJFIHGLIEBJ-UHFFFAOYSA-N 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- -1 sulfobenzoic acid compound Chemical class 0.000 claims description 15
- 229910001510 metal chloride Inorganic materials 0.000 claims description 14
- 230000002378 acidificating effect Effects 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- XWEBTVZIZWEJOO-UHFFFAOYSA-N 3-chlorosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 XWEBTVZIZWEJOO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical group O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 claims description 4
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- KQHKITXZJDOIOD-UHFFFAOYSA-M sodium;3-sulfobenzoate Chemical compound [Na+].OS(=O)(=O)C1=CC=CC(C([O-])=O)=C1 KQHKITXZJDOIOD-UHFFFAOYSA-M 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000012320 chlorinating reagent Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical class OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- LETZORNQQJXNMJ-UHFFFAOYSA-N 3-chloro-5-chlorosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=CC(S(Cl)(=O)=O)=C1 LETZORNQQJXNMJ-UHFFFAOYSA-N 0.000 description 1
- JYJUMAFOXPQPAU-UHFFFAOYSA-N 4-chlorosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JYJUMAFOXPQPAU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 C#*c1cc(C(O)=O)cc(C(O)=O)c1 Chemical compound C#*c1cc(C(O)=O)cc(C(O)=O)c1 0.000 description 1
- YUTBZLIYSBSIJR-UHFFFAOYSA-N C1=CC(=C(C=C1Cl)C(=O)Cl)S(=O)(=O)Cl Chemical compound C1=CC(=C(C=C1Cl)C(=O)Cl)S(=O)(=O)Cl YUTBZLIYSBSIJR-UHFFFAOYSA-N 0.000 description 1
- ZXEMJODUKSTXHI-UHFFFAOYSA-M C1=CC(=C(C=C1Cl)C(=O)[O-])S(=O)(=O)O.[K+] Chemical compound C1=CC(=C(C=C1Cl)C(=O)[O-])S(=O)(=O)O.[K+] ZXEMJODUKSTXHI-UHFFFAOYSA-M 0.000 description 1
- DTCLSOVJEXPOGN-UHFFFAOYSA-M C1=CC(=C(C=C1[N+](=O)[O-])C(=O)[O-])S(=O)(=O)O.[K+] Chemical compound C1=CC(=C(C=C1[N+](=O)[O-])C(=O)[O-])S(=O)(=O)O.[K+] DTCLSOVJEXPOGN-UHFFFAOYSA-M 0.000 description 1
- VAXDAFTZKDVYTK-UHFFFAOYSA-M CC1=CC(=C(C=C1)S(=O)(=O)O)C(=O)[O-].[K+] Chemical compound CC1=CC(=C(C=C1)S(=O)(=O)O)C(=O)[O-].[K+] VAXDAFTZKDVYTK-UHFFFAOYSA-M 0.000 description 1
- PCPVODYECWIYOV-UHFFFAOYSA-M CC1=CC(=CC(=C1)S(=O)(=O)O)C(=O)[O-].[Na+] Chemical compound CC1=CC(=CC(=C1)S(=O)(=O)O)C(=O)[O-].[Na+] PCPVODYECWIYOV-UHFFFAOYSA-M 0.000 description 1
- MQMQICJHUWHQQA-UHFFFAOYSA-N CC1=CC(C(Cl)=O)=CC(S(Cl)(=O)=O)=C1 Chemical compound CC1=CC(C(Cl)=O)=CC(S(Cl)(=O)=O)=C1 MQMQICJHUWHQQA-UHFFFAOYSA-N 0.000 description 1
- MISOIPNFQJZJCX-UHFFFAOYSA-N CCC1=CC(=C(C=C1)S(=O)(=O)Cl)C(=O)Cl Chemical compound CCC1=CC(=C(C=C1)S(=O)(=O)Cl)C(=O)Cl MISOIPNFQJZJCX-UHFFFAOYSA-N 0.000 description 1
- BCJAQLLIWIFMRF-UHFFFAOYSA-N CCC1=CC(=C(C=C1)S(=O)(=O)O)C(=O)O Chemical compound CCC1=CC(=C(C=C1)S(=O)(=O)O)C(=O)O BCJAQLLIWIFMRF-UHFFFAOYSA-N 0.000 description 1
- RMOTXPZQSBXLOK-UHFFFAOYSA-M CCC1=CC(=C(C=C1)S(=O)(=O)O)C(=O)[O-].[K+] Chemical compound CCC1=CC(=C(C=C1)S(=O)(=O)O)C(=O)[O-].[K+] RMOTXPZQSBXLOK-UHFFFAOYSA-M 0.000 description 1
- GUOLNGWTJXXKIH-UHFFFAOYSA-N CCC1=CC(=CC(=C1)S(=O)(=O)Cl)C(=O)Cl Chemical compound CCC1=CC(=CC(=C1)S(=O)(=O)Cl)C(=O)Cl GUOLNGWTJXXKIH-UHFFFAOYSA-N 0.000 description 1
- BURFNCKUQWENAN-UHFFFAOYSA-M COC1=CC(=CC(=C1)C(=O)[O-])S(=O)(=O)O.[Na+] Chemical compound COC1=CC(=CC(=C1)C(=O)[O-])S(=O)(=O)O.[Na+] BURFNCKUQWENAN-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IWYZHESLTJVRLG-UHFFFAOYSA-N ClS(=O)(=O)C=1C=C(C=C(C(=O)Cl)C=1)OC Chemical compound ClS(=O)(=O)C=1C=C(C=C(C(=O)Cl)C=1)OC IWYZHESLTJVRLG-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JPPYSPAXPNNOBC-UHFFFAOYSA-N O=C(c1cc(C(Cl)=O)cc(S(Cl)(=O)=O)c1)Cl Chemical compound O=C(c1cc(C(Cl)=O)cc(S(Cl)(=O)=O)c1)Cl JPPYSPAXPNNOBC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
- ZSUUCLLIOSUIFH-UHFFFAOYSA-N n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(C)=O ZSUUCLLIOSUIFH-UHFFFAOYSA-N 0.000 description 1
- UNBDDZDKBWPHAX-UHFFFAOYSA-N n,n-di(propan-2-yl)formamide Chemical compound CC(C)N(C=O)C(C)C UNBDDZDKBWPHAX-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FGHSTPNOXKDLKU-UHFFFAOYSA-N nitric acid;hydrate Chemical compound O.O[N+]([O-])=O FGHSTPNOXKDLKU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- CTBNLJAFVUHSEF-UHFFFAOYSA-M potassium;2-carboxy-4-methoxybenzenesulfonate Chemical compound [K+].COC1=CC=C(S([O-])(=O)=O)C(C(O)=O)=C1 CTBNLJAFVUHSEF-UHFFFAOYSA-M 0.000 description 1
- ZJVMUAMBOGFWRS-UHFFFAOYSA-M potassium;2-carboxy-5-nitrobenzenesulfonate Chemical compound [K+].OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1C([O-])=O ZJVMUAMBOGFWRS-UHFFFAOYSA-M 0.000 description 1
- JMCGARBKIAJZLC-UHFFFAOYSA-M potassium;2-sulfobenzoate Chemical compound [K+].OC(=O)C1=CC=CC=C1S([O-])(=O)=O JMCGARBKIAJZLC-UHFFFAOYSA-M 0.000 description 1
- PXRJBUPXKDXDLG-UHFFFAOYSA-M potassium;4-sulfobenzoate Chemical compound [K+].OC(=O)C1=CC=C(S([O-])(=O)=O)C=C1 PXRJBUPXKDXDLG-UHFFFAOYSA-M 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011240058A JP5795519B2 (ja) | 2011-11-01 | 2011-11-01 | クロロスルホニルベンゾイルクロライド化合物の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011240058A JP5795519B2 (ja) | 2011-11-01 | 2011-11-01 | クロロスルホニルベンゾイルクロライド化合物の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013095703A JP2013095703A (ja) | 2013-05-20 |
| JP2013095703A5 JP2013095703A5 (OSRAM) | 2014-11-27 |
| JP5795519B2 true JP5795519B2 (ja) | 2015-10-14 |
Family
ID=48618026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011240058A Expired - Fee Related JP5795519B2 (ja) | 2011-11-01 | 2011-11-01 | クロロスルホニルベンゾイルクロライド化合物の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5795519B2 (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR103071A1 (es) * | 2014-12-30 | 2017-04-12 | Dow Global Technologies Llc | Proceso para producir anhídrido 4-azidosulfonilftálico |
| TW201700458A (zh) | 2015-04-24 | 2017-01-01 | 第一三共股份有限公司 | 二羧酸化合物之製法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5262241A (en) * | 1975-11-19 | 1977-05-23 | Ihara Chem Ind Co Ltd | Preparation of chlorosulfonylbenzoyl chlorides |
| GB2005667B (en) * | 1977-10-03 | 1982-03-17 | Hooker Chemicals Plastics Corp | Process for the preparation of benzoyl halide and halosulftonylbenzoul halide |
| HU209288B (en) * | 1988-12-07 | 1994-04-28 | Ici America Inc | A new method for producing 2-(chlorine, bromine or nitro)-4-(chlorine-sulfonyl)-benzoyl-chloride |
| JP2001302612A (ja) * | 2000-04-24 | 2001-10-31 | Fuji Photo Film Co Ltd | ハロスルホニル安息香酸エステル類の製造方法 |
| DE10218704B4 (de) * | 2002-04-26 | 2006-11-30 | Bayer Cropscience Gmbh | Halosulfonylbenzoesäurehalogenide, Verfahren zu deren Herstellung und deren Verwendung zur Herstellung von substituierten Phenylsulfonylharnstoffen |
| CN101550097B (zh) * | 2009-05-14 | 2012-10-31 | 杭州水处理技术研究开发中心有限公司 | 5-氯磺酰异酞酰氯的制备方法 |
-
2011
- 2011-11-01 JP JP2011240058A patent/JP5795519B2/ja not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| JP2013095703A (ja) | 2013-05-20 |
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