JPH0586767B2 - - Google Patents
Info
- Publication number
- JPH0586767B2 JPH0586767B2 JP2305186A JP2305186A JPH0586767B2 JP H0586767 B2 JPH0586767 B2 JP H0586767B2 JP 2305186 A JP2305186 A JP 2305186A JP 2305186 A JP2305186 A JP 2305186A JP H0586767 B2 JPH0586767 B2 JP H0586767B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- groups
- general formula
- aryl
- 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 - Lifetime
Links
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- UWDCUCCPBLHLTI-UHFFFAOYSA-N 1-fluoropyridin-1-ium Chemical class F[N+]1=CC=CC=C1 UWDCUCCPBLHLTI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005142 aryl oxy sulfonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- QTJXVIKNLHZIKL-UHFFFAOYSA-N sulfur difluoride Chemical compound FSF QTJXVIKNLHZIKL-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 229910052731 fluorine Inorganic materials 0.000 description 15
- 239000011737 fluorine Substances 0.000 description 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- -1 phenyl α-chlorobenzyl sulfide Chemical compound 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011775 sodium fluoride Substances 0.000 description 3
- 235000013024 sodium fluoride Nutrition 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KIQQUVJOLVCZKG-UHFFFAOYSA-N 1-chloro-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(Cl)C=C1 KIQQUVJOLVCZKG-UHFFFAOYSA-N 0.000 description 2
- JFUKDQISVXMNRI-UHFFFAOYSA-M 1-fluoro-2,4,6-trimethylpyridin-1-ium;fluoride Chemical compound [F-].CC1=CC(C)=[N+](F)C(C)=C1 JFUKDQISVXMNRI-UHFFFAOYSA-M 0.000 description 2
- OFQPKKGMNWASPN-UHFFFAOYSA-N Benzyl methyl sulfide Chemical compound CSCC1=CC=CC=C1 OFQPKKGMNWASPN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- XGPOMXSYOKFBHS-UHFFFAOYSA-M sodium;trifluoromethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)F XGPOMXSYOKFBHS-UHFFFAOYSA-M 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- JMWLQGNTPBIYIE-UHFFFAOYSA-N 1-chloro-4-(fluoromethylsulfanyl)benzene Chemical compound FCSC1=CC=C(Cl)C=C1 JMWLQGNTPBIYIE-UHFFFAOYSA-N 0.000 description 1
- PRIGFEJKMMRJSF-UHFFFAOYSA-M 1-fluoro-2,4,6-trimethylpyridin-1-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC1=CC(C)=[N+](F)C(C)=C1 PRIGFEJKMMRJSF-UHFFFAOYSA-M 0.000 description 1
- BHWJMPDCCDMCKC-UHFFFAOYSA-N 1-methyl-2-methylsulfanylbenzene Chemical compound CSC1=CC=CC=C1C BHWJMPDCCDMCKC-UHFFFAOYSA-N 0.000 description 1
- AHCJTMBRROLNHV-UHFFFAOYSA-N 1-methylsulfanyloctane Chemical compound CCCCCCCCSC AHCJTMBRROLNHV-UHFFFAOYSA-N 0.000 description 1
- VWRNGTRNWYKKJE-UHFFFAOYSA-N 1-phenylpropane-2-thione Chemical compound CC(=S)CC1=CC=CC=C1 VWRNGTRNWYKKJE-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- INDWVHABTMSBCJ-UHFFFAOYSA-N 3-methylsulfanylpropanenitrile Chemical compound CSCCC#N INDWVHABTMSBCJ-UHFFFAOYSA-N 0.000 description 1
- RPVGEEHGKIFQFO-UHFFFAOYSA-N 4-methylsulfanylbenzonitrile Chemical compound CSC1=CC=C(C#N)C=C1 RPVGEEHGKIFQFO-UHFFFAOYSA-N 0.000 description 1
- AMQQWFLSHDKPPI-UHFFFAOYSA-N 4-phenylsulfanylbutan-2-one Chemical compound CC(=O)CCSC1=CC=CC=C1 AMQQWFLSHDKPPI-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RAFKCLFWELPONH-UHFFFAOYSA-N acetonitrile;dichloromethane Chemical compound CC#N.ClCCl RAFKCLFWELPONH-UHFFFAOYSA-N 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- JTWJOQUJCWRSAH-UHFFFAOYSA-N diethyl 2-methylsulfanylpropanedioate Chemical compound CCOC(=O)C(SC)C(=O)OCC JTWJOQUJCWRSAH-UHFFFAOYSA-N 0.000 description 1
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- VCXUFKFNLUTDAX-UHFFFAOYSA-N ethyl 3-(3-ethoxy-3-oxopropyl)sulfanylpropanoate Chemical compound CCOC(=O)CCSCCC(=O)OCC VCXUFKFNLUTDAX-UHFFFAOYSA-N 0.000 description 1
- YSNWHRKJEKWJNY-UHFFFAOYSA-N ethyl 3-(methylthio)propionate Chemical compound CCOC(=O)CCSC YSNWHRKJEKWJNY-UHFFFAOYSA-N 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GRAAOQUKOGOXJR-YFKPBYRVSA-N methyl (2s)-4-methylsulfanyl-2-[(2,2,2-trifluoroacetyl)amino]butanoate Chemical compound CSCC[C@@H](C(=O)OC)NC(=O)C(F)(F)F GRAAOQUKOGOXJR-YFKPBYRVSA-N 0.000 description 1
- CPQDZXPLQXZJGF-UHFFFAOYSA-N methyl 2-methylsulfanylbenzoate Chemical compound COC(=O)C1=CC=CC=C1SC CPQDZXPLQXZJGF-UHFFFAOYSA-N 0.000 description 1
- RDFKUOFSLFTQBK-UHFFFAOYSA-N methyl 3-oxo-2-phenylsulfanylbutanoate Chemical compound COC(=O)C(C(C)=O)SC1=CC=CC=C1 RDFKUOFSLFTQBK-UHFFFAOYSA-N 0.000 description 1
- VHILIAIEEYLJNA-UHFFFAOYSA-N methyl p-tolyl sulfide Chemical compound CSC1=CC=C(C)C=C1 VHILIAIEEYLJNA-UHFFFAOYSA-N 0.000 description 1
- SQEGSJWWDCTFEN-UHFFFAOYSA-N o-methyl 2-phenylethanethioate Chemical compound COC(=S)CC1=CC=CC=C1 SQEGSJWWDCTFEN-UHFFFAOYSA-N 0.000 description 1
- RVEBJDGWKWKYBH-UHFFFAOYSA-N o-methyl propanethioate Chemical compound CCC(=S)OC RVEBJDGWKWKYBH-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QGNRLAFFKKBSIM-UHFFFAOYSA-N prop-2-enylsulfanylbenzene Chemical compound C=CCSC1=CC=CC=C1 QGNRLAFFKKBSIM-UHFFFAOYSA-N 0.000 description 1
- HXKVNRKJSSHQQY-UHFFFAOYSA-N prop-2-ynylsulfanylbenzene Chemical compound C#CCSC1=CC=CC=C1 HXKVNRKJSSHQQY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Cephalosporin Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2305186A JPS62181230A (ja) | 1986-02-06 | 1986-02-06 | α−フルオロスルフイドの製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2305186A JPS62181230A (ja) | 1986-02-06 | 1986-02-06 | α−フルオロスルフイドの製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62181230A JPS62181230A (ja) | 1987-08-08 |
| JPH0586767B2 true JPH0586767B2 (enrdf_load_stackoverflow) | 1993-12-14 |
Family
ID=12099643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2305186A Granted JPS62181230A (ja) | 1986-02-06 | 1986-02-06 | α−フルオロスルフイドの製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62181230A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07233097A (ja) * | 1994-02-23 | 1995-09-05 | Chichibu Onoda Cement Corp | 親電子型フッ素化剤の製造方法 |
| FR2730993B1 (fr) * | 1995-02-28 | 1997-04-04 | Rhone Poulenc Chimie | Procede de synthese de compose hydrocarbone fluore sur un carbone d'une chaine alcoyle |
| JP6976678B2 (ja) * | 2016-05-10 | 2021-12-08 | ダイキン工業株式会社 | 含フッ素化合物、及びその製造方法 |
-
1986
- 1986-02-06 JP JP2305186A patent/JPS62181230A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62181230A (ja) | 1987-08-08 |
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