CA1071651A

CA1071651A - Styrylamidines

Styrylamidines

Info

Publication number: CA1071651A
Authority: CA; Canada
Prior art keywords: pharmaceutically acceptable; acid addition; benzamidine; addition salt; acceptable acid
Prior art date: 1974-04-08
Legal status : Expired

Application number

CA221,801A

Other languages

English (en)

French (fr)

Inventor

William L. Matier

William T. Comer

Current Assignee

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Squibb Co

Priority date

1974-04-08

Filing date

1975-03-11

Publication date

1980-02-12

1975-03-11 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1980-02-12 Application granted granted Critical

1980-02-12 Publication of CA1071651A publication Critical patent/CA1071651A/en

Status Expired legal-status Critical Current

Links

ONQNCCKCGKJMIA-UHFFFAOYSA-N n'-[2-(3,4-dichlorophenyl)ethenyl]ethanimidamide Chemical compound CC(=N)NC=CC1=CC=C(Cl)C(Cl)=C1 ONQNCCKCGKJMIA-UHFFFAOYSA-N 0.000 claims abstract 3
VGWLQQGTEQDNIR-UHFFFAOYSA-N n'-(2-phenylethenylsulfonyl)ethanimidamide Chemical group CC(=N)NS(=O)(=O)C=CC1=CC=CC=C1 VGWLQQGTEQDNIR-UHFFFAOYSA-N 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 131
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 120
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 92
239000002253 acid Substances 0.000 claims description 74
150000003839 salts Chemical class 0.000 claims description 72
231100000252 nontoxic Toxicity 0.000 claims description 65
230000003000 nontoxic effect Effects 0.000 claims description 65
230000008569 process Effects 0.000 claims description 65
-1 nitro, amino Chemical group 0.000 claims description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
238000002360 preparation method Methods 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 22
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 22
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 14
229910000033 sodium borohydride Inorganic materials 0.000 claims description 14
239000012279 sodium borohydride Substances 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
125000002905 alkanoylamido group Chemical group 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
GDYXPZCCNRBQNS-VOTSOKGWSA-N (e)-3-phenylprop-2-enimidamide Chemical compound NC(=N)\C=C\C1=CC=CC=C1 GDYXPZCCNRBQNS-VOTSOKGWSA-N 0.000 claims description 7
UICWNFKZDPYAGX-UHFFFAOYSA-N 4-nitro-n'-[2-(4-nitrophenyl)ethenyl]benzenecarboximidamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CNC(=N)C1=CC=C([N+]([O-])=O)C=C1 UICWNFKZDPYAGX-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
MSBPGJBBOKMEEC-UHFFFAOYSA-N n'-[2-(4-nitrophenyl)ethenyl]benzenecarboximidamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CNC(=N)C1=CC=CC=C1 MSBPGJBBOKMEEC-UHFFFAOYSA-N 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
GETXUHFWGKSGLH-UHFFFAOYSA-N 3-nitro-n'-[2-(4-nitrophenyl)ethenyl]benzenecarboximidamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CNC(=N)C1=CC=CC([N+]([O-])=O)=C1 GETXUHFWGKSGLH-UHFFFAOYSA-N 0.000 claims description 4
PZBVZYDYVORQQS-UHFFFAOYSA-N 4-(dimethylamino)-n'-[2-(4-nitrophenyl)ethenyl]benzenecarboximidamide Chemical compound C1=CC(N(C)C)=CC=C1C(=N)NC=CC1=CC=C([N+]([O-])=O)C=C1 PZBVZYDYVORQQS-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
JSWAISAZQRWURF-UHFFFAOYSA-N n'-[2-(2-nitrophenyl)ethenyl]benzenecarboximidamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C=CNC(=N)C1=CC=CC=C1 JSWAISAZQRWURF-UHFFFAOYSA-N 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000005504 styryl group Chemical group 0.000 claims description 4
CGYNWYTZQCJBBM-UHFFFAOYSA-N 3-amino-n'-[2-(4-aminophenyl)ethenyl]benzenecarboximidamide Chemical compound C1=CC(N)=CC=C1C=CNC(=N)C1=CC=CC(N)=C1 CGYNWYTZQCJBBM-UHFFFAOYSA-N 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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 3
MQXHXONBEDEVBK-UHFFFAOYSA-N n'-(2-phenylethenyl)ethanimidamide Chemical compound CC(=N)NC=CC1=CC=CC=C1 MQXHXONBEDEVBK-UHFFFAOYSA-N 0.000 claims description 3
RGRLHZJDLYHMNH-UHFFFAOYSA-N n'-[2-(4-aminophenyl)ethenyl]naphthalene-2-carboximidamide Chemical compound C1=CC(N)=CC=C1C=CNC(=N)C1=CC=C(C=CC=C2)C2=C1 RGRLHZJDLYHMNH-UHFFFAOYSA-N 0.000 claims description 3
XDVBBUGBUPIBHF-UHFFFAOYSA-N 4-amino-n'-[2-(4-nitrophenyl)ethenylsulfonyl]benzenecarboximidamide Chemical compound C1=CC(N)=CC=C1C(=N)NS(=O)(=O)C=CC1=CC=C([N+]([O-])=O)C=C1 XDVBBUGBUPIBHF-UHFFFAOYSA-N 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
XHQCAGPHQUGVSC-UHFFFAOYSA-N n'-[2-(2-nitrophenyl)ethenylsulfonyl]ethanimidamide Chemical compound CC(=N)NS(=O)(=O)C=CC1=CC=CC=C1[N+]([O-])=O XHQCAGPHQUGVSC-UHFFFAOYSA-N 0.000 claims description 2
CKLHZNADXIFHQY-UHFFFAOYSA-N n'-[2-(4-nitrophenyl)ethenyl]naphthalene-2-carboximidamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CNC(=N)C1=CC=C(C=CC=C2)C2=C1 CKLHZNADXIFHQY-UHFFFAOYSA-N 0.000 claims description 2
CXPVHRKCSBHULG-UHFFFAOYSA-N 3,5-diamino-n'-[2-(4-nitrophenyl)ethenyl]benzenecarboximidamide Chemical compound NC1=CC(N)=CC(C(=N)NC=CC=2C=CC(=CC=2)[N+]([O-])=O)=C1 CXPVHRKCSBHULG-UHFFFAOYSA-N 0.000 claims 3
XRELOZDVKJSRRB-UHFFFAOYSA-N n'-[2-(4-aminophenyl)ethenyl]benzenecarboximidamide Chemical compound C1=CC(N)=CC=C1C=CNC(=N)C1=CC=CC=C1 XRELOZDVKJSRRB-UHFFFAOYSA-N 0.000 claims 3
KSTXJSZWYSYTPW-UHFFFAOYSA-N 3,5-diamino-n'-[2-(4-aminophenyl)ethenyl]benzenecarboximidamide Chemical compound C1=CC(N)=CC=C1C=CNC(=N)C1=CC(N)=CC(N)=C1 KSTXJSZWYSYTPW-UHFFFAOYSA-N 0.000 claims 2
UYSRUBRQPYMEAZ-UHFFFAOYSA-N 3-amino-n'-[2-(4-nitrophenyl)ethenyl]benzenecarboximidamide Chemical compound NC1=CC=CC(C(=N)NC=CC=2C=CC(=CC=2)[N+]([O-])=O)=C1 UYSRUBRQPYMEAZ-UHFFFAOYSA-N 0.000 claims 2
YTKQCRUSZRZVDI-UHFFFAOYSA-N 4-amino-n'-[2-(4-aminophenyl)ethenyl]benzenecarboximidamide Chemical compound C1=CC(N)=CC=C1C=CNC(=N)C1=CC=C(N)C=C1 YTKQCRUSZRZVDI-UHFFFAOYSA-N 0.000 claims 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
FEYQKOFEKAZCAW-UHFFFAOYSA-N n'-(2-phenylethenyl)benzenecarboximidamide Chemical compound C=1C=CC=CC=1C(=N)NC=CC1=CC=CC=C1 FEYQKOFEKAZCAW-UHFFFAOYSA-N 0.000 claims 2
JTEAIYHECUZEOE-UHFFFAOYSA-N n'-[2-(2,6-dichlorophenyl)ethenyl]ethanimidamide Chemical compound CC(=N)NC=CC1=C(Cl)C=CC=C1Cl JTEAIYHECUZEOE-UHFFFAOYSA-N 0.000 claims 2
MGULHOBFBAIYQM-UHFFFAOYSA-N n'-[2-(2-aminophenyl)ethenyl]benzenecarboximidamide Chemical compound NC1=CC=CC=C1C=CNC(=N)C1=CC=CC=C1 MGULHOBFBAIYQM-UHFFFAOYSA-N 0.000 claims 2
FXRNEHAQMWXHLJ-UHFFFAOYSA-N n'-[2-(2-nitrophenyl)ethenyl]ethanimidamide Chemical compound CC(=N)NC=CC1=CC=CC=C1[N+]([O-])=O FXRNEHAQMWXHLJ-UHFFFAOYSA-N 0.000 claims 2
OHLWJEBTRWUQTA-UHFFFAOYSA-N n'-[2-(3,4-dichlorophenyl)ethenyl]-2-phenylethanimidamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C=CNC(=N)CC1=CC=CC=C1 OHLWJEBTRWUQTA-UHFFFAOYSA-N 0.000 claims 2
PTKZHLNWZIKPQI-UHFFFAOYSA-N n'-[2-(3,4-dichlorophenyl)ethenyl]-3,4-dimethoxybenzenecarboximidamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=N)NC=CC1=CC=C(Cl)C(Cl)=C1 PTKZHLNWZIKPQI-UHFFFAOYSA-N 0.000 claims 2
HCOQXKYFLRATOX-UHFFFAOYSA-N n'-[2-(3,4-dichlorophenyl)ethenyl]benzenecarboximidamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C=CNC(=N)C1=CC=CC=C1 HCOQXKYFLRATOX-UHFFFAOYSA-N 0.000 claims 2
MGQHFDXXVMASCC-UHFFFAOYSA-N n'-[2-(3-bromo-4-cyclohexylphenyl)ethenyl]ethanimidamide Chemical compound BrC1=CC(C=CNC(=N)C)=CC=C1C1CCCCC1 MGQHFDXXVMASCC-UHFFFAOYSA-N 0.000 claims 2
MRONHEKWGZSSOX-UHFFFAOYSA-N n'-[2-(4-chlorophenyl)ethenyl]ethanimidamide Chemical compound CC(=N)NC=CC1=CC=C(Cl)C=C1 MRONHEKWGZSSOX-UHFFFAOYSA-N 0.000 claims 2
MNUXGZIRYFSKMX-UHFFFAOYSA-N n'-[2-(4-nitrophenyl)ethenyl]ethanimidamide Chemical compound CC(=N)NC=CC1=CC=C([N+]([O-])=O)C=C1 MNUXGZIRYFSKMX-UHFFFAOYSA-N 0.000 claims 2
VNKKYVJALJWBJB-UHFFFAOYSA-N n-[4-[2-[[amino(phenyl)methylidene]amino]ethenyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C=CNC(=N)C1=CC=CC=C1 VNKKYVJALJWBJB-UHFFFAOYSA-N 0.000 claims 2
QGLKRTLGKZUMJE-UHFFFAOYSA-N n-methyl-n-[2-(4-nitrophenyl)ethenyl]benzenecarboximidamide Chemical compound C=1C=CC=CC=1C(=N)N(C)C=CC1=CC=C([N+]([O-])=O)C=C1 QGLKRTLGKZUMJE-UHFFFAOYSA-N 0.000 claims 2
JHTYQOXVIIPLIE-UHFFFAOYSA-N 3,5-diamino-n'-[2-(4-nitrophenyl)ethenylsulfonyl]benzenecarboximidamide Chemical compound NC1=CC(N)=CC(C(=N)NS(=O)(=O)C=CC=2C=CC(=CC=2)[N+]([O-])=O)=C1 JHTYQOXVIIPLIE-UHFFFAOYSA-N 0.000 claims 1
KEPVCCCQNXNUAU-UHFFFAOYSA-N 3-amino-n'-[2-(4-nitrophenyl)ethenylsulfonyl]benzenecarboximidamide Chemical compound NC1=CC=CC(C(=N)NS(=O)(=O)C=CC=2C=CC(=CC=2)[N+]([O-])=O)=C1 KEPVCCCQNXNUAU-UHFFFAOYSA-N 0.000 claims 1
ZEWCYMYPXPNRCQ-UHFFFAOYSA-N 3-nitro-n'-[2-(4-nitrophenyl)ethenylsulfonyl]benzenecarboximidamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CS(=O)(=O)NC(=N)C1=CC=CC([N+]([O-])=O)=C1 ZEWCYMYPXPNRCQ-UHFFFAOYSA-N 0.000 claims 1
GUICLIDYGDCUMI-UHFFFAOYSA-N 4-(dimethylamino)-n'-[2-(4-nitrophenyl)ethenylsulfonyl]benzenecarboximidamide Chemical compound C1=CC(N(C)C)=CC=C1C(=N)NS(=O)(=O)C=CC1=CC=C([N+]([O-])=O)C=C1 GUICLIDYGDCUMI-UHFFFAOYSA-N 0.000 claims 1
NKKGUHQTANAQIQ-UHFFFAOYSA-N 4-nitro-n'-[2-(4-nitrophenyl)ethenylsulfonyl]benzenecarboximidamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CS(=O)(=O)NC(=N)C1=CC=C([N+]([O-])=O)C=C1 NKKGUHQTANAQIQ-UHFFFAOYSA-N 0.000 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
ZPKYNUJZUXVAIH-UHFFFAOYSA-N CN(C(=N)C1=CC=CC=C1)S(=O)(=O)C=CC2=CC=C(C=C2)[N+](=O)[O-] Chemical compound CN(C(=N)C1=CC=CC=C1)S(=O)(=O)C=CC2=CC=C(C=C2)[N+](=O)[O-] ZPKYNUJZUXVAIH-UHFFFAOYSA-N 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
UUANXALULUSAQZ-UHFFFAOYSA-N n'-[2-(2,6-dichlorophenyl)ethenylsulfonyl]ethanimidamide Chemical compound CC(=N)NS(=O)(=O)C=CC1=C(Cl)C=CC=C1Cl UUANXALULUSAQZ-UHFFFAOYSA-N 0.000 claims 1
BZIYWUSGMBDYCU-UHFFFAOYSA-N n'-[2-(2-nitrophenyl)ethenylsulfonyl]benzenecarboximidamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C=CS(=O)(=O)NC(=N)C1=CC=CC=C1 BZIYWUSGMBDYCU-UHFFFAOYSA-N 0.000 claims 1
ZHVBUNXWENSNCY-UHFFFAOYSA-N n'-[2-(3,4-dichlorophenyl)ethenylsulfonyl]-2-phenylethanimidamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C=CS(=O)(=O)NC(=N)CC1=CC=CC=C1 ZHVBUNXWENSNCY-UHFFFAOYSA-N 0.000 claims 1
JAAXVPDNIZJJPA-UHFFFAOYSA-N n'-[2-(3,4-dichlorophenyl)ethenylsulfonyl]-3,4-dimethoxybenzenecarboximidamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=N)NS(=O)(=O)C=CC1=CC=C(Cl)C(Cl)=C1 JAAXVPDNIZJJPA-UHFFFAOYSA-N 0.000 claims 1
OGDKXKQFHJZFJU-UHFFFAOYSA-N n'-[2-(3,4-dichlorophenyl)ethenylsulfonyl]benzenecarboximidamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C=CS(=O)(=O)NC(=N)C1=CC=CC=C1 OGDKXKQFHJZFJU-UHFFFAOYSA-N 0.000 claims 1
HYQOPXONCRVZIP-UHFFFAOYSA-N n'-[2-(3,4-dichlorophenyl)ethenylsulfonyl]ethanimidamide Chemical compound CC(=N)NS(=O)(=O)C=CC1=CC=C(Cl)C(Cl)=C1 HYQOPXONCRVZIP-UHFFFAOYSA-N 0.000 claims 1
DZRRNTCHDIYUSW-UHFFFAOYSA-N n'-[2-(3-bromo-4-cyclohexylphenyl)ethenylsulfonyl]ethanimidamide Chemical compound BrC1=CC(C=CS(=O)(=O)NC(=N)C)=CC=C1C1CCCCC1 DZRRNTCHDIYUSW-UHFFFAOYSA-N 0.000 claims 1
DWMXRQXURQVWNB-UHFFFAOYSA-N n'-[2-(4-chlorophenyl)ethenylsulfonyl]ethanimidamide Chemical compound CC(=N)NS(=O)(=O)C=CC1=CC=C(Cl)C=C1 DWMXRQXURQVWNB-UHFFFAOYSA-N 0.000 claims 1
BAQRNZBUHCSAHC-UHFFFAOYSA-N n'-[2-(4-nitrophenyl)ethenyl]-3-phenylprop-2-enimidamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C=CN=C(N)C=CC1=CC=CC=C1 BAQRNZBUHCSAHC-UHFFFAOYSA-N 0.000 claims 1
ZNODEHZBLWOGCC-UHFFFAOYSA-N n'-[2-(4-nitrophenyl)ethenylsulfonyl]-3-phenylprop-2-enimidamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C=CS(=O)(=O)N=C(N)C=CC1=CC=CC=C1 ZNODEHZBLWOGCC-UHFFFAOYSA-N 0.000 claims 1
NEHXUXOKTMUEBO-UHFFFAOYSA-N n'-[2-(4-nitrophenyl)ethenylsulfonyl]benzenecarboximidamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CS(=O)(=O)NC(=N)C1=CC=CC=C1 NEHXUXOKTMUEBO-UHFFFAOYSA-N 0.000 claims 1
FGQARERFBYCWNI-UHFFFAOYSA-N n'-[2-(4-nitrophenyl)ethenylsulfonyl]ethanimidamide Chemical compound CC(=N)NS(=O)(=O)C=CC1=CC=C([N+]([O-])=O)C=C1 FGQARERFBYCWNI-UHFFFAOYSA-N 0.000 claims 1
239000012429 reaction media Substances 0.000 claims 1
230000000202 analgesic effect Effects 0.000 abstract description 9
239000002243 precursor Substances 0.000 abstract description 6
210000001772 blood platelet Anatomy 0.000 abstract description 4
230000002776 aggregation Effects 0.000 abstract description 2
238000004220 aggregation Methods 0.000 abstract description 2
230000002265 prevention Effects 0.000 abstract 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
239000012458 free base Substances 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
238000004458 analytical method Methods 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 20
229910000041 hydrogen chloride Inorganic materials 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
235000011121 sodium hydroxide Nutrition 0.000 description 18
229940083608 sodium hydroxide Drugs 0.000 description 18
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
150000001409 amidines Chemical class 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
SVMBRAHBRXXFEU-UHFFFAOYSA-N 2-(4-nitrophenyl)ethenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C=CS(Cl)(=O)=O)C=C1 SVMBRAHBRXXFEU-UHFFFAOYSA-N 0.000 description 8
RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
230000009467 reduction Effects 0.000 description 8
238000006722 reduction reaction Methods 0.000 description 8
BJQFWAQRPATHTR-UHFFFAOYSA-N 1,2-dichloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1Cl BJQFWAQRPATHTR-UHFFFAOYSA-N 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
238000001665 trituration Methods 0.000 description 7
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
230000002965 anti-thrombogenic effect Effects 0.000 description 6
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