SK2122003A3 - Aminoalkoxybenzoyl-benzofuran or benzothiophene derivatives, method for preparing same and compositions containing same - Google Patents

Info

Publication number

SK2122003A3

SK2122003A3 SK212-2003A SK2122003A SK2122003A3 SK 2122003 A3 SK2122003 A3 SK 2122003A3 SK 2122003 A SK2122003 A SK 2122003A SK 2122003 A3 SK2122003 A3 SK 2122003A3

Authority

SK

Slovakia

Prior art keywords

group

formula

alkali metal

carbon atoms

compound

Prior art date

2000-08-23

Links

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• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title claims abstract description 42
• 239000000203 mixture Substances 0.000 title claims description 59
• 238000000034 method Methods 0.000 title claims description 45
• 150000001875 compounds Chemical class 0.000 claims abstract description 421
• 239000003814 drug Substances 0.000 claims abstract description 5
• 230000001575 pathological effect Effects 0.000 claims abstract description 5
• 210000000748 cardiovascular system Anatomy 0.000 claims abstract description 4
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 108
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 93
• 229910052783 alkali metal Inorganic materials 0.000 claims description 93
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 90
• 229910052721 tungsten Inorganic materials 0.000 claims description 89
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 80
• 239000012458 free base Substances 0.000 claims description 76
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 46
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
• 238000006243 chemical reaction Methods 0.000 claims description 41
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
• -1 diethylpiperidyl group Chemical group 0.000 claims description 41
• 239000002585 base Substances 0.000 claims description 39
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
• 125000003277 amino group Chemical group 0.000 claims description 31
• 239000003795 chemical substances by application Substances 0.000 claims description 31
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 30
• 239000002253 acid Substances 0.000 claims description 30
• 238000002360 preparation method Methods 0.000 claims description 29
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
• 230000008569 process Effects 0.000 claims description 25
• 150000007522 mineralic acids Chemical class 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 22
• 150000007524 organic acids Chemical class 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 19
• 150000001340 alkali metals Chemical class 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
• 239000003054 catalyst Substances 0.000 claims description 14
• 238000010511 deprotection reaction Methods 0.000 claims description 14
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 14
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
• 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 12
• 150000008041 alkali metal carbonates Chemical class 0.000 claims description 12
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
• 150000001412 amines Chemical class 0.000 claims description 11
• 230000002140 halogenating effect Effects 0.000 claims description 11
• 239000001257 hydrogen Substances 0.000 claims description 11
• 150000001266 acyl halides Chemical class 0.000 claims description 10
• 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 239000004480 active ingredient Substances 0.000 claims description 7
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
• 239000003153 chemical reaction reagent Substances 0.000 claims description 6
• 150000004820 halides Chemical class 0.000 claims description 6
• 150000002576 ketones Chemical class 0.000 claims description 6
• 125000005936 piperidyl group Chemical group 0.000 claims description 6
• 125000006239 protecting group Chemical group 0.000 claims description 6
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 4
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
• 239000002841 Lewis acid Substances 0.000 claims description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
• 150000001263 acyl chlorides Chemical class 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 229910052796 boron Inorganic materials 0.000 claims description 4
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
• 150000007517 lewis acids Chemical class 0.000 claims description 4
• 150000002923 oximes Chemical class 0.000 claims description 4
• 230000002829 reductive effect Effects 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
• 206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 3
• 206010019280 Heart failures Diseases 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
• 239000004472 Lysine Substances 0.000 claims description 3
• APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 claims description 3
• 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 3
• 235000010323 ascorbic acid Nutrition 0.000 claims description 3
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 3
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 3
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 3
• LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 230000002861 ventricular Effects 0.000 claims description 3
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
• 206010002383 Angina Pectoris Diseases 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• 206010065929 Cardiovascular insufficiency Diseases 0.000 claims description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
• 229910019142 PO4 Inorganic materials 0.000 claims description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• 206010042600 Supraventricular arrhythmias Diseases 0.000 claims description 2
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
• 150000008064 anhydrides Chemical class 0.000 claims description 2
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
• CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical class N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 claims description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 230000002490 cerebral effect Effects 0.000 claims description 2
• 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 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
• AFAXGSQYZLGZPG-UHFFFAOYSA-L ethanedisulfonate group Chemical class C(CS(=O)(=O)[O-])S(=O)(=O)[O-] AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 claims description 2
• IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical compound C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 claims description 2
• 150000002306 glutamic acid derivatives Chemical class 0.000 claims description 2
• 125000004997 halocarbonyl group Chemical group 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• 150000003840 hydrochlorides Chemical class 0.000 claims description 2
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
• 208000010125 myocardial infarction Diseases 0.000 claims description 2
• 150000002823 nitrates Chemical class 0.000 claims description 2
• 150000002828 nitro derivatives Chemical class 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical class NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 150000002942 palmitic acid derivatives Chemical class 0.000 claims description 2
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
• 235000021317 phosphate Nutrition 0.000 claims description 2
• 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
• 230000002265 prevention Effects 0.000 claims description 2
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
• IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 2
• 239000011593 sulfur Substances 0.000 claims description 2
• 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 150000003573 thiols Chemical class 0.000 claims description 2
• 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 2
• HQALDKFFRYFTKP-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzothiophen-3-yl)phenyl]-2-bromo-6-(3-methoxyphenyl)phenoxy]acetic acid Chemical compound COC1=CC=CC(C=2C(=C(Br)C=C(C=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3SC=2CC=2C=CC=CC=2)OCC(O)=O)=C1 HQALDKFFRYFTKP-UHFFFAOYSA-N 0.000 claims 6
• 150000002431 hydrogen Chemical class 0.000 claims 5
• 125000002843 carboxylic acid group Chemical group 0.000 claims 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
• 150000002484 inorganic compounds Chemical class 0.000 claims 2
• 229910010272 inorganic material Inorganic materials 0.000 claims 2
• 150000002894 organic compounds Chemical class 0.000 claims 2
• 150000003873 salicylate salts Chemical class 0.000 claims 2
• 150000000994 L-ascorbates Chemical class 0.000 claims 1
• 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
• 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 1
• 150000001413 amino acids Chemical class 0.000 claims 1
• JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 claims 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
• 230000000747 cardiac effect Effects 0.000 claims 1
• 150000001860 citric acid derivatives Chemical class 0.000 claims 1
• 230000007812 deficiency Effects 0.000 claims 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims 1
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
• 150000003893 lactate salts Chemical class 0.000 claims 1
• 229940049920 malate Drugs 0.000 claims 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 claims 1
• 150000002688 maleic acid derivatives Chemical class 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
• WBDPHWBGJQIYDK-UHFFFAOYSA-N methyl 2-phenyl-3-[4-(2-piperidin-1-ylethoxy)benzoyl]-1-benzothiophene-6-carboxylate Chemical compound C=1C=CC=CC=1C=1SC2=CC(C(=O)OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 WBDPHWBGJQIYDK-UHFFFAOYSA-N 0.000 claims 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• 150000003891 oxalate salts Chemical class 0.000 claims 1
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
• 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
• 150000003890 succinate salts Chemical class 0.000 claims 1
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 1
• 210000004243 sweat Anatomy 0.000 claims 1
• 150000003892 tartrate salts Chemical class 0.000 claims 1
• JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 claims 1
• 229940079593 drug Drugs 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 252
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 189
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 153
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 151
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 121
• 239000000243 solution Substances 0.000 description 100
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 98
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 97
• 239000011541 reaction mixture Substances 0.000 description 84
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 50
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• 239000003480 eluent Substances 0.000 description 48
• 238000004587 chromatography analysis Methods 0.000 description 45
• 239000000377 silicon dioxide Substances 0.000 description 45
• 238000005481 NMR spectroscopy Methods 0.000 description 36
• 239000000047 product Substances 0.000 description 32
• 238000000746 purification Methods 0.000 description 31
• 239000002904 solvent Substances 0.000 description 31
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
• 239000007787 solid Substances 0.000 description 26
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 26
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
• 238000010992 reflux Methods 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
• 238000005406 washing Methods 0.000 description 19
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 18
• 238000009835 boiling Methods 0.000 description 18
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• 239000000284 extract Substances 0.000 description 15
• 238000000605 extraction Methods 0.000 description 15
• 235000006408 oxalic acid Nutrition 0.000 description 15
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
• 238000012360 testing method Methods 0.000 description 15
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 14
• 238000002425 crystallisation Methods 0.000 description 14
• 230000008025 crystallization Effects 0.000 description 14
• 239000012074 organic phase Substances 0.000 description 14
• 229910000027 potassium carbonate Inorganic materials 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
• 239000012267 brine Substances 0.000 description 13
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
• 235000017557 sodium bicarbonate Nutrition 0.000 description 12
• 238000001704 evaporation Methods 0.000 description 11
• 230000008020 evaporation Effects 0.000 description 11
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• 239000012071 phase Substances 0.000 description 10
• CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 10
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• 239000008346 aqueous phase Substances 0.000 description 9
• 150000008282 halocarbons Chemical class 0.000 description 9
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