DE1445409C3 - - Google Patents
Info
- Publication number
- DE1445409C3 DE1445409C3 DE19621445409 DE1445409A DE1445409C3 DE 1445409 C3 DE1445409 C3 DE 1445409C3 DE 19621445409 DE19621445409 DE 19621445409 DE 1445409 A DE1445409 A DE 1445409A DE 1445409 C3 DE1445409 C3 DE 1445409C3
- Authority
- DE
- Germany
- Prior art keywords
- amino
- phenyl
- oxadiazole
- group
- mole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 13
- 239000008096 xylene Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 9
- DZHVJUCGKWKRTO-UHFFFAOYSA-N 3-phenyl-1,2,4-oxadiazol-5-amine Chemical class O1C(N)=NC(C=2C=CC=CC=2)=N1 DZHVJUCGKWKRTO-UHFFFAOYSA-N 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 239000011874 heated mixture Substances 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 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 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 206010052895 Coronary artery insufficiency Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000003589 local anesthetic agent Substances 0.000 claims 1
- 229960005015 local anesthetics Drugs 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- -1 (2-diethylamino-ethyl) -amino Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 2
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 description 1
- GVWMHLCBIUIASU-UHFFFAOYSA-N 1-chloro-n,n-dimethylethanamine Chemical compound CC(Cl)N(C)C GVWMHLCBIUIASU-UHFFFAOYSA-N 0.000 description 1
- PUNDBTKEOORSOO-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropan-2-amine Chemical compound CN(C)C(C)(C)Cl PUNDBTKEOORSOO-UHFFFAOYSA-N 0.000 description 1
- WVUULNDRFBHTFG-UHFFFAOYSA-N 3-chloro-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCCl WVUULNDRFBHTFG-UHFFFAOYSA-N 0.000 description 1
- SBVJBGYORWPSMC-UHFFFAOYSA-N CC(CN(C)C)NC1=NC(C2=CC=CC=C2)=NO1 Chemical compound CC(CN(C)C)NC1=NC(C2=CC=CC=C2)=NO1 SBVJBGYORWPSMC-UHFFFAOYSA-N 0.000 description 1
- CJEPVWDMZRGXKC-UHFFFAOYSA-N CCCCN(CCCC)CCCNC1=NC(C2=CC=CC=C2)=NO1 Chemical compound CCCCN(CCCC)CCCNC1=NC(C2=CC=CC=C2)=NO1 CJEPVWDMZRGXKC-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- BHFWYLYNEWCFEG-UHFFFAOYSA-N N',N'-dimethyl-N-(3-phenyl-1,2,4-oxadiazol-5-yl)propane-1,3-diamine Chemical compound O1C(NCCCN(C)C)=NC(C=2C=CC=CC=2)=N1 BHFWYLYNEWCFEG-UHFFFAOYSA-N 0.000 description 1
- VWXUXMOEXHJNLX-UHFFFAOYSA-N NC1=NOC(CCNN2CCCCC2)=N1 Chemical compound NC1=NOC(CCNN2CCCCC2)=N1 VWXUXMOEXHJNLX-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- HFXOMPIWXDVHSZ-UHFFFAOYSA-N n',n'-diethyl-n-(3-phenyl-1,2,4-oxadiazol-5-yl)ethane-1,2-diamine Chemical compound O1C(NCCN(CC)CC)=NC(C=2C=CC=CC=2)=N1 HFXOMPIWXDVHSZ-UHFFFAOYSA-N 0.000 description 1
- LZAZIXFGGIZJBK-UHFFFAOYSA-N n',n'-dimethyl-n-(3-phenyl-1,2,4-oxadiazol-5-yl)ethane-1,2-diamine Chemical compound O1C(NCCN(C)C)=NC(C=2C=CC=CC=2)=N1 LZAZIXFGGIZJBK-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2511661 | 1962-06-12 | ||
| DEA0040651 | 1962-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1445409C3 true DE1445409C3 (enrdf_load_stackoverflow) | 1976-12-30 |
Family
ID=
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