DE2506330A1 - Verfahren zur herstellung von enolderivaten - Google Patents

Info

Publication number

DE2506330A1

DE2506330A1 DE19752506330 DE2506330A DE2506330A1 DE 2506330 A1 DE2506330 A1 DE 2506330A1 DE 19752506330 DE19752506330 DE 19752506330 DE 2506330 A DE2506330 A DE 2506330A DE 2506330 A1 DE2506330 A1 DE 2506330A1

Authority

DE

Germany

Prior art keywords

group

acid

formula

methoxy

compounds

Prior art date

1974-02-26

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.)

Ceased

Links

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• 238000000034 method Methods 0.000 title claims description 108
• 230000008569 process Effects 0.000 title claims description 23
• 238000004519 manufacturing process Methods 0.000 title description 7
• 150000002085 enols Chemical class 0.000 title description 5
• -1 benzyloxy, p-nitrobenzyloxy Chemical group 0.000 claims description 978
• 150000001875 compounds Chemical class 0.000 claims description 177
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 145
• 239000000203 mixture Substances 0.000 claims description 136
• 125000000217 alkyl group Chemical group 0.000 claims description 117
• 239000002253 acid Substances 0.000 claims description 109
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 105
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 101
• 150000003839 salts Chemical class 0.000 claims description 101
• 125000003545 alkoxy group Chemical group 0.000 claims description 89
• 229910052739 hydrogen Inorganic materials 0.000 claims description 79
• 239000001257 hydrogen Substances 0.000 claims description 79
• 125000003118 aryl group Chemical group 0.000 claims description 67
• 125000001931 aliphatic group Chemical group 0.000 claims description 64
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
• 229910052736 halogen Inorganic materials 0.000 claims description 62
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 58
• 150000002367 halogens Chemical class 0.000 claims description 57
• 238000006243 chemical reaction Methods 0.000 claims description 53
• 125000002252 acyl group Chemical group 0.000 claims description 51
• 239000000460 chlorine Substances 0.000 claims description 48
• 150000002148 esters Chemical class 0.000 claims description 48
• 239000003795 chemical substances by application Substances 0.000 claims description 47
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
• 229910052757 nitrogen Inorganic materials 0.000 claims description 45
• 150000002431 hydrogen Chemical class 0.000 claims description 40
• 229910052801 chlorine Inorganic materials 0.000 claims description 39
• 125000004432 carbon atom Chemical group C* 0.000 claims description 38
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
• 239000007858 starting material Substances 0.000 claims description 38
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 36
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 35
• 125000003277 amino group Chemical group 0.000 claims description 35
• 229930195733 hydrocarbon Natural products 0.000 claims description 35
• 239000004215 Carbon black (E152) Substances 0.000 claims description 34
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
• 125000006239 protecting group Chemical group 0.000 claims description 32
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 28
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 claims description 24
• 125000004423 acyloxy group Chemical group 0.000 claims description 21
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 20
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
• SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical class S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 claims description 18
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 18
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
• 229910052794 bromium Inorganic materials 0.000 claims description 18
• 125000000524 functional group Chemical group 0.000 claims description 18
• 239000003638 chemical reducing agent Substances 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 239000011737 fluorine Substances 0.000 claims description 15
• 229910052731 fluorine Inorganic materials 0.000 claims description 15
• 125000004442 acylamino group Chemical group 0.000 claims description 14
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 14
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 13
• 150000003973 alkyl amines Chemical class 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 11
• 125000005103 alkyl silyl group Chemical group 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 11
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 238000006266 etherification reaction Methods 0.000 claims description 10
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 10
• 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 claims description 10
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 10
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• 230000002829 reductive effect Effects 0.000 claims description 8
• 239000011593 sulfur Substances 0.000 claims description 8
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 7
• 125000004104 aryloxy group Chemical group 0.000 claims description 7
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 230000007062 hydrolysis Effects 0.000 claims description 7
• 238000006460 hydrolysis reaction Methods 0.000 claims description 7
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 7
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 7
• ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 7
• 125000004149 thio group Chemical group *S* 0.000 claims description 7
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 6
• 150000003949 imides Chemical class 0.000 claims description 6
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 claims description 5
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 238000006136 alcoholysis reaction Methods 0.000 claims description 5
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 5
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
• 239000007795 chemical reaction product Substances 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000004494 ethyl ester group Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 150000002430 hydrocarbons Chemical group 0.000 claims description 4
• 239000011630 iodine Chemical group 0.000 claims description 4
• 229910052740 iodine Chemical group 0.000 claims description 4
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 4
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
• 125000003441 thioacyl group Chemical group 0.000 claims description 4
• KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 3
• ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 claims description 3
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
• 125000006016 2-bromoethoxy group Chemical group 0.000 claims description 3
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
• 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
• 238000000855 fermentation Methods 0.000 claims description 3
• 230000004151 fermentation Effects 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 2
• SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 2
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 claims description 2
• 150000002357 guanidines Chemical class 0.000 claims description 2
• 239000013067 intermediate product Substances 0.000 claims description 2
• LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical class C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 claims description 2
• PFZCOWLKXHIVII-UHFFFAOYSA-N pyridin-1-ium-1-amine Chemical group N[N+]1=CC=CC=C1 PFZCOWLKXHIVII-UHFFFAOYSA-N 0.000 claims description 2
• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
• 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims 1
• PBJBVIHLBRYRQC-UHFFFAOYSA-N 1-o-[2-(diethylamino)ethyl] 3-o-ethyl 2-methyl-2-phenylpropanedioate Chemical compound CCN(CC)CCOC(=O)C(C)(C(=O)OCC)C1=CC=CC=C1 PBJBVIHLBRYRQC-UHFFFAOYSA-N 0.000 claims 1
• BILUQVOMCIHWNX-UHFFFAOYSA-N 3-methyl-2-[2-(4-methylphenyl)sulfonylsulfanyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]but-3-enoic acid Chemical compound C=1C=CC=CC=1CC(=O)NC1C(=O)N(C(C(=C)C)C(O)=O)C1SS(=O)(=O)C1=CC=C(C)C=C1 BILUQVOMCIHWNX-UHFFFAOYSA-N 0.000 claims 1
• 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
• WAVQOKDKPHYRDY-GOSISDBHSA-N benzhydryl (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C([C@H]1SCC=2)C(=O)N1C=2C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 WAVQOKDKPHYRDY-GOSISDBHSA-N 0.000 claims 1
• XPDGOAYDTHKGJD-OXQOHEQNSA-N benzhydryl (6r,7r)-7-amino-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S([C@H]1N2C([C@H]1N)=O)CC(OC)=C2C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 XPDGOAYDTHKGJD-OXQOHEQNSA-N 0.000 claims 1
• QDGLDXWIBIDNSB-BUHFOSPRSA-N benzhydryl (E)-3-methoxybut-2-enoate Chemical compound C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(\C=C(/C)\OC)=O QDGLDXWIBIDNSB-BUHFOSPRSA-N 0.000 claims 1
• 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 248
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 231
• 239000000243 solution Substances 0.000 description 155
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 143
• 235000002639 sodium chloride Nutrition 0.000 description 90
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 87
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 86
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 78
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
• 150000003254 radicals Chemical class 0.000 description 69
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 57
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
• 239000000741 silica gel Substances 0.000 description 52
• 229910002027 silica gel Inorganic materials 0.000 description 52
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
• 239000002904 solvent Substances 0.000 description 51
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 46
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 39
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 38
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
• 235000019441 ethanol Nutrition 0.000 description 37
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 36
• 238000002844 melting Methods 0.000 description 35
• 230000008018 melting Effects 0.000 description 35
• 238000003756 stirring Methods 0.000 description 31
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
• 229960000583 acetic acid Drugs 0.000 description 29
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 28
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
• 239000002585 base Substances 0.000 description 26
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 26
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• 238000002329 infrared spectrum Methods 0.000 description 25
• 239000012074 organic phase Substances 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 23
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
• 229910052938 sodium sulfate Inorganic materials 0.000 description 23
• 235000011152 sodium sulphate Nutrition 0.000 description 23
• 150000007513 acids Chemical class 0.000 description 22
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 21
• 230000002378 acidificating effect Effects 0.000 description 21
• 229910052783 alkali metal Inorganic materials 0.000 description 20
• 238000001816 cooling Methods 0.000 description 20
• 235000017557 sodium bicarbonate Nutrition 0.000 description 20
• 239000012299 nitrogen atmosphere Substances 0.000 description 19
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
• 239000002244 precipitate Substances 0.000 description 18
• 150000008064 anhydrides Chemical group 0.000 description 17
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 17
• KWPQTFXULUUCGD-UHFFFAOYSA-N 3,4,5,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCN=CC2CCCCN21 KWPQTFXULUUCGD-UHFFFAOYSA-N 0.000 description 16
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 16
• 229910001385 heavy metal Inorganic materials 0.000 description 16
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
• 239000010410 layer Substances 0.000 description 15
• 125000001424 substituent group Chemical group 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 14
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• 125000003375 sulfoxide group Chemical group 0.000 description 1
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• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
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• 238000012360 testing method Methods 0.000 description 1
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• 229930101283 tetracycline Natural products 0.000 description 1
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• HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
• YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical group [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
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• YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
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• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
• GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
• FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
• 230000001256 tonic effect Effects 0.000 description 1
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• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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• ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
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• OLBXOAKEHMWSOV-UHFFFAOYSA-N triethyltin;hydrate Chemical compound O.CC[Sn](CC)CC OLBXOAKEHMWSOV-UHFFFAOYSA-N 0.000 description 1
• HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
• JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
• NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 238000010626 work up procedure Methods 0.000 description 1