JPWO2008032463A1 - スルホン酸エステルの製造法 - Google Patents
スルホン酸エステルの製造法 Download PDFInfo
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- JPWO2008032463A1 JPWO2008032463A1 JP2008534251A JP2008534251A JPWO2008032463A1 JP WO2008032463 A1 JPWO2008032463 A1 JP WO2008032463A1 JP 2008534251 A JP2008534251 A JP 2008534251A JP 2008534251 A JP2008534251 A JP 2008534251A JP WO2008032463 A1 JPWO2008032463 A1 JP WO2008032463A1
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- -1 sulfonate ester Chemical class 0.000 title claims abstract description 1048
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 125000003118 aryl group Chemical group 0.000 claims abstract description 38
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 28
- 125000005843 halogen group Chemical group 0.000 claims abstract description 27
- 150000007530 organic bases Chemical class 0.000 claims abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 140
- 125000001424 substituent group Chemical group 0.000 claims description 88
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 125000002252 acyl group Chemical group 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 9
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 claims description 3
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 claims description 3
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- 150000004693 imidazolium salts Chemical class 0.000 claims 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000002253 acid Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 150000002500 ions Chemical class 0.000 description 29
- 125000003277 amino group Chemical group 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 229910052731 fluorine Inorganic materials 0.000 description 17
- 125000001153 fluoro group Chemical group F* 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
- 239000012043 crude product Substances 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 11
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 11
- 229910052740 iodine Inorganic materials 0.000 description 11
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 10
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 10
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 10
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 10
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 9
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 9
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 9
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 8
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 7
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 230000000704 physical effect Effects 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
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- JDQNYWYMNFRKNQ-UHFFFAOYSA-N 3-ethyl-4-methylpyridine Chemical compound CCC1=CN=CC=C1C JDQNYWYMNFRKNQ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 6
- 150000003459 sulfonic acid esters Chemical class 0.000 description 6
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 5
- 125000005999 2-bromoethyl group Chemical group 0.000 description 5
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 5
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 125000005997 bromomethyl group Chemical group 0.000 description 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 5
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 5
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 5
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 5
- 125000005008 perfluoropentyl group Chemical group FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 5
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 5
- GWAOOGWHPITOEY-UHFFFAOYSA-N 1,5,2,4-dioxadithiane 2,2,4,4-tetraoxide Chemical compound O=S1(=O)CS(=O)(=O)OCO1 GWAOOGWHPITOEY-UHFFFAOYSA-N 0.000 description 4
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 4
- KNCHDRLWPAKSII-UHFFFAOYSA-N 4-ethyl-2-methylpyridine Chemical compound CCC1=CC=NC(C)=C1 KNCHDRLWPAKSII-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- 125000003368 amide group Chemical class 0.000 description 4
- 125000001124 arachidoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 4
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 description 4
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 4
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 4
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 4
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 4
- 125000005921 isopentoxy group Chemical group 0.000 description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000006606 n-butoxy group Chemical group 0.000 description 4
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 4
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 4
- 125000005484 neopentoxy group Chemical group 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
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- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
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- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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- CELGOKROJLHUIK-UHFFFAOYSA-N n,n-bis(2,2-dimethylpropyl)-2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN(CC(C)(C)C)CC(C)(C)C CELGOKROJLHUIK-UHFFFAOYSA-N 0.000 description 1
- SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- WYJGBGIMGDYEII-UHFFFAOYSA-N n,n-di(hexan-2-yl)hexan-2-amine Chemical compound CCCCC(C)N(C(C)CCCC)C(C)CCCC WYJGBGIMGDYEII-UHFFFAOYSA-N 0.000 description 1
- RGZUXCMJXPQZBT-UHFFFAOYSA-N n,n-di(pentan-2-yl)pentan-2-amine Chemical compound CCCC(C)N(C(C)CCC)C(C)CCC RGZUXCMJXPQZBT-UHFFFAOYSA-N 0.000 description 1
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
- FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 description 1
- NILJCGYQNXKIRL-UHFFFAOYSA-N n,n-dicyclopentylcyclopentanamine Chemical compound C1CCCC1N(C1CCCC1)C1CCCC1 NILJCGYQNXKIRL-UHFFFAOYSA-N 0.000 description 1
- QJEWDNDJRVJYBY-UHFFFAOYSA-N n,n-dicyclopropylcyclopropanamine Chemical compound C1CC1N(C1CC1)C1CC1 QJEWDNDJRVJYBY-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- IBEMVTXUBPIYEM-UHFFFAOYSA-N n,n-dinaphthalen-1-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(N(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 IBEMVTXUBPIYEM-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- CYQYCASVINMDFD-UHFFFAOYSA-N n,n-ditert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)N(C(C)(C)C)C(C)(C)C CYQYCASVINMDFD-UHFFFAOYSA-N 0.000 description 1
- VUXINUDYAQGLKJ-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CNCC(C)(C)C VUXINUDYAQGLKJ-UHFFFAOYSA-N 0.000 description 1
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
- NSNOXLZAKBVTDW-UHFFFAOYSA-N n-cyclobutylcyclobutanamine Chemical compound C1CCC1NC1CCC1 NSNOXLZAKBVTDW-UHFFFAOYSA-N 0.000 description 1
- FUUUBHCENZGYJA-UHFFFAOYSA-N n-cyclopentylcyclopentanamine Chemical compound C1CCCC1NC1CCCC1 FUUUBHCENZGYJA-UHFFFAOYSA-N 0.000 description 1
- JKWKFBUUNGGYBP-UHFFFAOYSA-N n-cyclopropylcyclopropanamine Chemical compound C1CC1NC1CC1 JKWKFBUUNGGYBP-UHFFFAOYSA-N 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- NQYKSVOHDVVDOR-UHFFFAOYSA-N n-hexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCC NQYKSVOHDVVDOR-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- ZZJKGVPMLGIOTF-UHFFFAOYSA-N n-pentan-2-ylpentan-2-amine Chemical compound CCCC(C)NC(C)CCC ZZJKGVPMLGIOTF-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- ZFIFHAKCBWOSRN-UHFFFAOYSA-N naphthalene-1-sulfonamide Chemical group C1=CC=C2C(S(=O)(=O)N)=CC=CC2=C1 ZFIFHAKCBWOSRN-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229940005654 nitrite ion Drugs 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HTKPDYSCAPSXIR-UHFFFAOYSA-N octyltrimethylammonium ion Chemical compound CCCCCCCC[N+](C)(C)C HTKPDYSCAPSXIR-UHFFFAOYSA-N 0.000 description 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- RJQRCOMHVBLQIH-UHFFFAOYSA-M pentane-1-sulfonate Chemical compound CCCCCS([O-])(=O)=O RJQRCOMHVBLQIH-UHFFFAOYSA-M 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- LLYCMZGLHLKPPU-UHFFFAOYSA-M perbromate Chemical compound [O-]Br(=O)(=O)=O LLYCMZGLHLKPPU-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
- QZHDEAJFRJCDMF-UHFFFAOYSA-N perfluorohexanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QZHDEAJFRJCDMF-UHFFFAOYSA-N 0.000 description 1
- CXZGQIAOTKWCDB-UHFFFAOYSA-N perfluoropentanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CXZGQIAOTKWCDB-UHFFFAOYSA-N 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-M periodate Chemical compound [O-]I(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-M 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical compound [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QLNJFJADRCOGBJ-LBPDFUHNSA-N propanamide Chemical group CC[13C](N)=O QLNJFJADRCOGBJ-LBPDFUHNSA-N 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UFWWAKOWSBGGCP-UHFFFAOYSA-N pyridine;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.C1=CC=NC=C1 UFWWAKOWSBGGCP-UHFFFAOYSA-N 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- NSRBDSZKIKAZHT-UHFFFAOYSA-N tellurium zinc Chemical compound [Zn].[Te] NSRBDSZKIKAZHT-UHFFFAOYSA-N 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- DNUYPCSVTPIXRE-UHFFFAOYSA-N tribromomethanesulfonic acid Chemical compound OS(=O)(=O)C(Br)(Br)Br DNUYPCSVTPIXRE-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- VYGSFTVYZHNGBU-UHFFFAOYSA-N trichloromethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Cl)Cl VYGSFTVYZHNGBU-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical group NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/30—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reactions not involving the formation of esterified sulfo groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/10—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms two oxygen atoms and one sulfur atom, e.g. cyclic sulfates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
このような状況下、目的とする各種スルホン酸エステルを高収率で効率的に製造する方法の開発が望まれている。
(ii)(a)一般式[6]で示されるジスルホン酸2当量以上と(b)一般式[5]で示される化合物1当量を反応させることにより得られる一般式[12]
(式中、R10〜R13は、夫々独立してアルキル基又はアラルキル基を表し、Aはカウンターアニオンを表す。また、R10〜R13のうちの3つとそれらが結合する窒素原子とでヘテロ環を形成していてもよい。)で示されるもの等が挙げられる。
反応後の後処理は、この分野に於いて通常行われる後処理法に準じて行えばよい。
ヘキサン (66mL)中に、ジヨードメタン (8.4g, 31.4mmol)及びトリフルオロメタンスルホン酸銀〔TfOAg〕(17.0g, 66.2mmol)を、65℃で8時間撹拌反応させ、メタンジトリフレート〔CF3SO2OCH2OSO2CF3〕を調製した。得られたメタンジトリフレート溶液に、アセトニトリル(66mL)及びメタンジスルホン酸ピリジニウム塩(10.0g, 29.9mmol)を加えて65℃で更に2時間反応させた。反応終了後、析出したヨウ化銀(13.4g, 57.1mmol)を濾別し、得られた反応液を減圧濃縮して黒褐色固体(21.3g)を得た。これをシリカゲルカラムクロマトグラフィー(酢酸エチル/ヘキサン=1/3)で精製し、目的のメチレンメタンジスルホネートを収率73%(4.1g, 21.8mmol)で単離した。
〔物性データ〕
1H-NMR (CD3CN) δ=5.30(s, 2H), 5.97(s, 2H)
13C-NMR (CD3CN) δ=68.9, 91.8
1-ブタンスルホン酸(10g, 0.072mol)を塩化メチレン(50mL)に溶解させ、次いでピリジン(11g, 0.14mol)を滴下し、室温で2時間反応させた。反応後、溶媒を減圧下で濃縮・乾固させ、1-ブタンスルホン酸ピリジニウム塩を含む粗製体を得た。この粗製体(5g, 0.023mol)をシクロヘキサン(50mL)に懸濁させ、ジメチル硫酸(15g, 0.12mol)を加えて、80℃で2時間反応させた。得られた反応液を減圧下で濃縮し、目的物である1-ブタンスルホン酸メチルエステルを得た。1H-NMRを用いて定量したところ、反応率は77%であった。
〔物性データ〕
1H-NMR (DMSO-d6) δ=0.90(t, J=7Hz, 3H), 1.42(m, 2H), 1.66(m, 2H), 3.31(dd, J=7.6Hz, 2H), 3.86(s, 3H).
アリルスルホン酸(10g, 0.082mol)を塩化メチレン(50mL)に溶解させ、ピリジン(11g, 0.14mol)を滴下し、室温で2時間反応させた。反応後、溶媒を減圧下で濃縮・乾固させ、アリルスルホン酸ピリジニウム塩を含む粗製体を得た。この粗製体(5g, 0.025mol)をシクロヘキサン(50mL)に懸濁させ、ジメチル硫酸(16g, 0.12mol)を加えて、80℃で2時間反応させた。反応液を減圧下で濃縮し、目的物であるアリルスルホン酸メチルエステルを得た。1H-NMRを用いて定量したところ、反応率は80%であった。
〔物性データ〕
1H-NMR (DMSO-d6) δ=3.89(s, 3H), 4.14(d, J=7Hz, 2H), 5.46(d, J=27Hz), 5.49(d, J=34Hz, 1H), 5.8(m, 1H).
塩化メチレン 50mL中、2-アミノベンゼンスルホン酸(10g, 0.058mol)とピリジン(10g, 0.13mol)を添加し、更にクロロ炭酸フェニル(14g, 0.087mol)を室温で滴下し、2時間反応させた。反応後、イオン交換水で水洗し、濃縮・乾固させ、2-(フェノキシカルボニルアミノ)ベンゼンスルホン酸を含む粗製体を得た。この粗製体(5g, 0.01mol)をシクロヘキサン(50mL)に懸濁させ、ジメチル硫酸(6.4g, 0.051mol)を加えて、80℃で2時間反応させた。反応液を減圧下で濃縮し、目的物である2-(フェノキシカルボニルアミノ)ベンゼンスルホン酸メチルエステルを得た。1H-NMRを用いて定量したところ、反応率は53%であった。
〔物性データ〕
1H-NMR (DMSO-d6) δ=4.00(s, 3H), 7.2-7.6(m, 4H), 7.7-8.1(m, 5H), 9.30(br s, 1H).
p-トルエンスルホン酸・2水和物(10g, 0.05mol)を塩化メチレン(50mL)に懸濁させ、ピリジン(5.1g, 0.06mol)を滴下し、室温で1時間反応させた。反応後、溶媒を減圧下で濃縮・乾固させ、p-トルエンスルホン酸ピリジニウム塩を含む粗製体を得た。この粗製体(5g, 0.020mol)をシクロヘキサン(50mL)に懸濁させ、ジメチル硫酸(5.0g, 0.040mol)を加えて、80℃で2時間反応させた。反応液を減圧下で濃縮し、目的物であるp-トルエンスルホン酸メチルエステルを得た。1H-NMRを用いて定量したところ、反応率は90%であった。
〔物性データ〕
1H-NMR (DMSO-d6) δ=2.43(s, 3H), 3.72(s, 3H), 7.45(d, J=8.4Hz), 7.72(d, J=8.4Hz, 2H).
p-トルエンスルホン酸・2水和物(10g, 0.05mol)を塩化メチレン(50mL)に懸濁させ、キノリン(8.3g, 0.06mol)を滴下し、室温で1時間反応させた。反応後、溶媒を減圧下で濃縮・乾固させ、p-トルエンスルホン酸キノリニウム塩を含む粗製体を得た。この粗製体(5g, 0.016mol)をシクロヘキサン(50mL)に懸濁させ、ジメチル硫酸(4.2g, 0.033mol)を加えて、80℃で2時間反応させた。反応液を減圧下で濃縮し、目的物であるp-トルエンスルホン酸メチルエステルを得た。1H-NMRを用いて定量したところ、反応率は93%であった。
p-トルエンスルホン酸・2水和物(10g, 0.05mol)を塩化メチレン(50mL)に懸濁させ、ジフェニルアミン(10.8g, 0.06mol)を滴下し、室温で1時間反応させた。反応後、溶媒を減圧下で濃縮・乾固させ、p-トルエンスルホン酸ジフェニルアンモニウム塩を含む粗製体を得た。この粗製体(5g, 0.011mol)をシクロヘキサン(50mL)に懸濁させ、ジメチル硫酸(3.0g, 0.023mol)を加えて、80℃で2時間反応させた。反応液を減圧下で濃縮し、目的物であるp-トルエンスルホン酸メチルエステルを得た。1H-NMRを用いて定量したところ、反応率は63%であった。
炭酸ジメチル(10mL)中、常法(例えば米国特許第4,649,209号公報等)に従って合成されたメチレンビス(クロロスルフェート)〔ClSO2OCH2OSO2Cl〕(1.5g, 6.1mmol)及びメタンジスルホン酸ピリジニウム塩(2.0g, 6.0mmol)を55℃で3時間撹拌反応させた。反応終了後、析出したクロロスルホン酸ピリジニウム塩を濾別し、得られた反応液を減圧濃縮して薄茶褐色固体(2.0g)を得た。これを1H-NMRを用いて定量したところ、目的物であるメチレンメタンジスルホネートの収率は76%であった。
〔物性データ〕
1H-NMR (CD3CN) δ=5.31(s, 2H), 5.97(s, 2H)
13C-NMR (CD3CN) δ=68.9, 91.8
実施例1〜8の結果から明らかなように、従来法よりも目的のスルホン酸エステルを高収率で得ることができた。
{式中、R 6 は一般式[1]で示される基、ハロゲン原子、炭素数1〜12のハロアルキル基、炭素数1〜12のアルキル基、炭素数6〜14のアリール基、炭素数1〜12のアルコキシ基、アシル基、ニトロ基、ヒドロキシル基、カルボキシル基、シアノ基、ホルミル基及びスルホ基から選ばれる置換基を有していてもよい炭素数1〜12のアルキル基を表し、m個のT 4 は夫々独立して、一般式[1]で示される基、ハロゲン原子、炭素数1〜12のハロアルキル基、炭素数1〜12のアルキル基、炭素数6〜14のアリール基、炭素数1〜12のアルコキシ基、アシル基、ニトロ基、ヒドロキシル基、カルボキシル基、シアノ基、ホルミル基及びスルホ基から選ばれる置換基を有していてもよい炭素数1〜8のアルキレン鎖を表し、m個のX 1 は夫々独立して酸素原子、硫黄原子又は一般式[25]
(式中、R 18 は炭素数1〜12のアルキル基、炭素数1〜12のハロアルキル基、炭素数6〜14のアリール基又は炭素数7〜15のアラルキル基を表す。)を表し、mは1〜6の整数を表す。}で示されるヘテロ原子含有アルキル基を表す。〕で示されるスルホ基含有化合物と
(b)一般式[5]
(式中、R 1 は一般式[2]で示されるスルホニル基を表し、R 5 は、一般式[1]で示される基、ハロゲン原子、炭素数6〜14のアリール基、炭素数7〜12のアラルキル基、炭素数1〜12のアルコキシ基、アシル基、置換されていてもよいアミノ基、シアノ基、ニトロ基、ヒドロキシル基、カルボキシル基、ホルミル基及びスルホ基から選ばれる置換基を有していてもよい、炭素数1〜12のアルキル基、炭素数2〜12のアルケニル基、炭素数2〜12のアルキニル基、炭素数6〜14のアリール基若しくはヘテロ環基、又は一般式[9]で示されるヘテロ原子含有アルキル基を表す。)で示される化合物とを、当該スルホ基と塩を形成し得る有機塩基の共存下で反応させることを特徴とする、スルホン酸エステル化合物の製造方法、の発明である。
【発明の効果】
塩化メチレン 50mL中、2-アミノベンゼンスルホン酸(10g, 0.058mol)とピリジン(10g, 0.13mol)を添加し、更にクロロ炭酸フェニル(14g, 0.087mol)を室温で滴下し、2時間反応させた。反応後、イオン交換水で水洗し、濃縮・乾固させ、2-(フェノキシカルボニルアミノ)ベンゼンスルホン酸を含む粗製体を得た。この粗製体(5g, 0.01mol)をシクロヘキサン(50mL)に懸濁させ、ジメチル硫酸(6.4g, 0.051mol)を加えて、80℃で2時間反応させた。反応液を減圧下で濃縮し、目的物である2-(フェノキシカルボニルアミノ)ベンゼンスルホン酸メチルエステルを得た。1H-NMRを用いて定量したところ、反応率は53%であった。
〔物性データ〕
1H-NMR (DMSO-d6) δ=4.00(s, 3H), 7.2-7.6(m, 4H), 7.7-8.1(m, 5H), 9.30(br s, 1H).
Claims (18)
- (a)スルホ基を有する化合物と当該スルホ基と塩を形成し得る有機塩基を混合させた後、次いで(b)一般式[1]で示される基を有する化合物を反応させるものである、請求項1に記載の製造法。
- T1及びT2が夫々独立して炭素数1〜8のアルキレン鎖である、請求項6に記載の製造法。
- T1及びT2がメチレン基である、請求項6に記載の製造法。
- R1が一般式[2]で示されるスルホニル基である、請求項6に記載の製造法。
- R1がクロロスルホニル基又はトリフルオロメタンスルホニル基である、請求項6に記載の製造法。
- 有機塩基が、第2級アミン、第3級アミン又は第4級アンモニウム塩である、請求項1、3〜6及び11の何れかに記載の製造法。
- 第3級アミンが、ピリジン、コリジン又はルチジンである、請求項12に記載の製造法。
- 第4級アンモニウム塩がピリジニウム塩又はイミダゾリウム塩である、請求項12に記載の製造法。
- 第4級アンモニウム塩のカウンターアニオンがハロゲン化物イオン又は水酸化物イオンである、請求項14に記載の製造法。
- 非水溶媒中で行う、請求項1に記載の製造法。
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EP2474527B1 (en) | 2009-08-31 | 2017-01-25 | Wako Pure Chemical Industries, Ltd. | Ionic liquid containing allylsulfonate anion |
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LAPS | Cancellation because of no payment of annual fees |