PL86679B1 - - Google Patents
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- Publication number
- PL86679B1 PL86679B1 PL1973163130A PL16313073A PL86679B1 PL 86679 B1 PL86679 B1 PL 86679B1 PL 1973163130 A PL1973163130 A PL 1973163130A PL 16313073 A PL16313073 A PL 16313073A PL 86679 B1 PL86679 B1 PL 86679B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- cresol
- alkoxy
- methoxy
- acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 7
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- FNQIBGUYHSFQLO-UHFFFAOYSA-N 2-methyl-5-nitrosophenol Chemical compound CC1=CC=C(N=O)C=C1O FNQIBGUYHSFQLO-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkyl mercaptan Chemical compound 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000006193 diazotization reaction Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims 1
- 229930003836 cresol Natural products 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- NFWPZNNZUCPLAX-UHFFFAOYSA-N 4-methoxy-3-methylaniline Chemical compound COC1=CC=C(N)C=C1C NFWPZNNZUCPLAX-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- BXWLVQXAFBWKSR-UHFFFAOYSA-N 2-methoxy-5-methylsulfonylbenzoic acid Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(O)=O BXWLVQXAFBWKSR-UHFFFAOYSA-N 0.000 description 3
- XXHQKVPWMWCBCH-UHFFFAOYSA-N 4-ethylsulfanyl-1-methoxy-2-methylbenzene Chemical compound CCSC1=CC=C(OC)C(C)=C1 XXHQKVPWMWCBCH-UHFFFAOYSA-N 0.000 description 3
- NBFYWQQYIJTQQV-UHFFFAOYSA-N 5-ethylsulfonyl-2-methoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 NBFYWQQYIJTQQV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- AIWIJSFUUKMEIC-UHFFFAOYSA-N 1-methoxy-2-methyl-4-methylsulfanylbenzene Chemical compound COC1=CC=C(SC)C=C1C AIWIJSFUUKMEIC-UHFFFAOYSA-N 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960003116 amyl nitrite Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- QYJXDIUNDMRLAO-UHFFFAOYSA-N butyl 4-methylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=C(C)C=C1 QYJXDIUNDMRLAO-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
- YSVZADAAWQNYCF-UHFFFAOYSA-N methylsulfanylmethane;sodium Chemical compound [Na].CSC YSVZADAAWQNYCF-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- ZJVTYKZWDWVIFD-UHFFFAOYSA-N zinc;hydrochloride Chemical compound Cl.[Zn] ZJVTYKZWDWVIFD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7221147A FR2188602A5 (Direct) | 1972-06-12 | 1972-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL86679B1 true PL86679B1 (Direct) | 1976-06-30 |
Family
ID=9100081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973163130A PL86679B1 (Direct) | 1972-06-12 | 1973-06-06 |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS4985044A (Direct) |
| KR (1) | KR780000268B1 (Direct) |
| AT (1) | AT321890B (Direct) |
| BE (1) | BE800751A (Direct) |
| BG (1) | BG20779A3 (Direct) |
| CA (1) | CA979003A (Direct) |
| CH (1) | CH568284A5 (Direct) |
| CS (1) | CS172980B2 (Direct) |
| DD (1) | DD104511A5 (Direct) |
| DE (1) | DE2328912A1 (Direct) |
| ES (1) | ES415726A1 (Direct) |
| FR (1) | FR2188602A5 (Direct) |
| GB (1) | GB1395295A (Direct) |
| IE (1) | IE37770B1 (Direct) |
| IL (1) | IL42457A (Direct) |
| IT (1) | IT1056041B (Direct) |
| LU (1) | LU67768A1 (Direct) |
| MC (1) | MC971A1 (Direct) |
| PH (1) | PH9257A (Direct) |
| PL (1) | PL86679B1 (Direct) |
| RO (1) | RO63838A (Direct) |
| YU (1) | YU35233B (Direct) |
| ZA (1) | ZA733928B (Direct) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2460922A1 (fr) * | 1979-07-06 | 1981-01-30 | Ile De France | Nouveaux acides 2-methoxy-4-nitro-5-alkylsulfonyl benzoiques, leur procedes de preparation et leur utilisation comme intermediaires de synthese de medicaments |
-
1972
- 1972-06-12 FR FR7221147A patent/FR2188602A5/fr not_active Expired
-
1973
- 1973-05-28 PH PH14663*UA patent/PH9257A/en unknown
- 1973-05-28 MC MC1047A patent/MC971A1/fr unknown
- 1973-06-06 GB GB2705073A patent/GB1395295A/en not_active Expired
- 1973-06-06 PL PL1973163130A patent/PL86679B1/pl unknown
- 1973-06-07 JP JP48064313A patent/JPS4985044A/ja active Pending
- 1973-06-07 KR KR7300906A patent/KR780000268B1/ko not_active Expired
- 1973-06-07 YU YU1523/73A patent/YU35233B/xx unknown
- 1973-06-07 IE IE922/73A patent/IE37770B1/xx unknown
- 1973-06-07 IL IL42457A patent/IL42457A/xx unknown
- 1973-06-08 AT AT505973A patent/AT321890B/de not_active IP Right Cessation
- 1973-06-08 LU LU67768A patent/LU67768A1/xx unknown
- 1973-06-08 ES ES415726A patent/ES415726A1/es not_active Expired
- 1973-06-08 DE DE2328912A patent/DE2328912A1/de active Pending
- 1973-06-08 IT IT50599/73A patent/IT1056041B/it active
- 1973-06-08 BG BG023829A patent/BG20779A3/xx unknown
- 1973-06-11 ZA ZA733928A patent/ZA733928B/xx unknown
- 1973-06-11 CS CS4199A patent/CS172980B2/cs unknown
- 1973-06-11 CA CA173,756A patent/CA979003A/en not_active Expired
- 1973-06-12 DD DD171476A patent/DD104511A5/xx unknown
- 1973-06-12 CH CH846673A patent/CH568284A5/xx not_active IP Right Cessation
- 1973-06-12 RO RO7300075110A patent/RO63838A/ro unknown
- 1973-06-12 BE BE1005139A patent/BE800751A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR780000268B1 (en) | 1978-07-24 |
| CA979003A (en) | 1975-12-02 |
| CS172980B2 (Direct) | 1977-01-28 |
| JPS4985044A (Direct) | 1974-08-15 |
| IE37770B1 (en) | 1977-10-12 |
| RO63838A (fr) | 1978-10-15 |
| CH568284A5 (Direct) | 1975-10-31 |
| IE37770L (en) | 1973-12-12 |
| YU152373A (en) | 1980-04-30 |
| FR2188602A5 (Direct) | 1974-01-18 |
| PH9257A (en) | 1975-07-30 |
| MC971A1 (fr) | 1974-02-01 |
| BE800751A (fr) | 1973-12-12 |
| IT1056041B (it) | 1982-01-30 |
| LU67768A1 (Direct) | 1974-07-05 |
| ZA733928B (en) | 1974-09-25 |
| GB1395295A (en) | 1975-05-21 |
| YU35233B (en) | 1980-10-31 |
| IL42457A (en) | 1975-12-31 |
| DE2328912A1 (de) | 1974-01-17 |
| DD104511A5 (Direct) | 1974-03-12 |
| BG20779A3 (bg) | 1975-12-20 |
| AT321890B (de) | 1975-04-25 |
| ES415726A1 (es) | 1976-02-01 |
| AU5666873A (en) | 1974-12-12 |
| IL42457A0 (en) | 1973-08-29 |
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