JPH0465068B2 - - Google Patents
Info
- Publication number
- JPH0465068B2 JPH0465068B2 JP1160480A JP1160480A JPH0465068B2 JP H0465068 B2 JPH0465068 B2 JP H0465068B2 JP 1160480 A JP1160480 A JP 1160480A JP 1160480 A JP1160480 A JP 1160480A JP H0465068 B2 JPH0465068 B2 JP H0465068B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- pyrimidinyl
- benzonitrile
- acid
- ester
- 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
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 358
- 239000000203 mixture Substances 0.000 claims description 221
- -1 trans-1,4-disubstituted cyclohexane ring Chemical group 0.000 claims description 182
- 239000002253 acid Substances 0.000 claims description 59
- 150000003230 pyrimidines Chemical class 0.000 claims description 53
- 239000000126 substance Substances 0.000 claims description 43
- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 37
- RGONNDWSVOCREF-UHFFFAOYSA-N 4-(5-pentylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCC)=CN=C1C1=CC=C(C#N)C=C1 RGONNDWSVOCREF-UHFFFAOYSA-N 0.000 claims description 36
- 239000004973 liquid crystal related substance Substances 0.000 claims description 32
- VSNGFYYRBATOTN-UHFFFAOYSA-N 4-(5-heptylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C#N)C=C1 VSNGFYYRBATOTN-UHFFFAOYSA-N 0.000 claims description 31
- JFKUBRAOUZEZSL-UHFFFAOYSA-N 4-butylbenzoic acid Chemical compound CCCCC1=CC=C(C(O)=O)C=C1 JFKUBRAOUZEZSL-UHFFFAOYSA-N 0.000 claims description 31
- RVLAXPQGTRTHEV-UHFFFAOYSA-N 4-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1CCC(C(O)=O)CC1 RVLAXPQGTRTHEV-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- ZGOWXOZNUNZPAV-UHFFFAOYSA-N 4-(4-heptylphenyl)benzonitrile Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 ZGOWXOZNUNZPAV-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 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 18
- 238000004040 coloring Methods 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- JRNQQLWJXYJSRU-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(C#N)C=C1 JRNQQLWJXYJSRU-JCNLHEQBSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- LXVTVIQMKOLVSY-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C(=O)OC1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C(=O)OC1=CC=C(C#N)C=C1 LXVTVIQMKOLVSY-CTYIDZIISA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- YAZXDRDFNUEKBH-KOMQPUFPSA-N C1C[C@@H](CC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 Chemical compound C1C[C@@H](CC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 YAZXDRDFNUEKBH-KOMQPUFPSA-N 0.000 claims description 9
- HJIVFZUPTYADSP-WKILWMFISA-N C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(OC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(OC)C=C1 HJIVFZUPTYADSP-WKILWMFISA-N 0.000 claims description 9
- XIXOFKHADLKBQN-UAPYVXQJSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 XIXOFKHADLKBQN-UAPYVXQJSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- LCDCOOLHWJZOQR-KOMQPUFPSA-N C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(C#N)C=C1 LCDCOOLHWJZOQR-KOMQPUFPSA-N 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 5
- VJMNQADPCKONIA-XUTJKUGGSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 VJMNQADPCKONIA-XUTJKUGGSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical class [H]C([H])([H])O* 0.000 claims description 4
- AITQOXOBSMXBRV-UHFFFAOYSA-N 4-[4-(4-pentylphenyl)phenyl]benzonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 AITQOXOBSMXBRV-UHFFFAOYSA-N 0.000 claims description 3
- ZAUPPIHFDVKVJM-IYARVYRRSA-N C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(OCCC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(OCCC)C=C1 ZAUPPIHFDVKVJM-IYARVYRRSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- GPGGNNIMKOVSAG-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 GPGGNNIMKOVSAG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims description 2
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000006609 n-nonyloxy group Chemical group 0.000 claims description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- JAYBMJPZPJBTQZ-WKILWMFISA-N C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(OCC)C=C1 JAYBMJPZPJBTQZ-WKILWMFISA-N 0.000 claims 10
- KAUZFALYEAHYIH-UHFFFAOYSA-N 2-[5-(4-ethylcyclohexyl)pyrimidin-2-yl]benzonitrile Chemical compound C1CC(CC)CCC1C1=CN=C(C=2C(=CC=CC=2)C#N)N=C1 KAUZFALYEAHYIH-UHFFFAOYSA-N 0.000 claims 3
- SGJSQQLUMMGQOS-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#C[C]1CCCCC1 SGJSQQLUMMGQOS-UHFFFAOYSA-N 0.000 claims 2
- FRLVVPHULLQDHW-UHFFFAOYSA-N (4-methoxyphenyl) cyclohexanecarboxylate Chemical compound C1=CC(OC)=CC=C1OC(=O)C1CCCCC1 FRLVVPHULLQDHW-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 123
- 230000008018 melting Effects 0.000 description 123
- 150000002148 esters Chemical class 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 238000003756 stirring Methods 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 13
- BALGERHMIXFENA-UHFFFAOYSA-N 4-butylcyclohexane-1-carboxylic acid Chemical compound CCCCC1CCC(C(O)=O)CC1 BALGERHMIXFENA-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
- FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- QCNUKEGGHOLBES-UHFFFAOYSA-N 4-propylcyclohexane-1-carboxylic acid Chemical compound CCCC1CCC(C(O)=O)CC1 QCNUKEGGHOLBES-UHFFFAOYSA-N 0.000 description 7
- 241000577218 Phenes Species 0.000 description 7
- 230000003098 cholesteric effect Effects 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 244000201986 Cassia tora Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 125000003944 tolyl group Chemical group 0.000 description 6
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- FVVOVPSXICDNRE-UHFFFAOYSA-N 4-heptan-3-ylbenzonitrile Chemical compound CCCCC(CC)c1ccc(cc1)C#N FVVOVPSXICDNRE-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 239000003990 capacitor Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 4
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 2
- 125000005917 3-methylpentyl group Chemical group 0.000 description 2
- CSQPODPWWMOTIY-UHFFFAOYSA-N 4-(4-octylphenyl)benzonitrile Chemical group C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 CSQPODPWWMOTIY-UHFFFAOYSA-N 0.000 description 2
- GQJHPVOLXNKXKB-UHFFFAOYSA-N 4-[5-(4-butylphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(CCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 GQJHPVOLXNKXKB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FWTDIYXSNMNJJI-SAABIXHNSA-N C1=CC(CCC)=CC=C1C1=CN=C([C@@H]2CC[C@H](CC2)C#N)N=C1 Chemical compound C1=CC(CCC)=CC=C1C1=CN=C([C@@H]2CC[C@H](CC2)C#N)N=C1 FWTDIYXSNMNJJI-SAABIXHNSA-N 0.000 description 2
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- VODOKUNOGBXWEX-JCNLHEQBSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 VODOKUNOGBXWEX-JCNLHEQBSA-N 0.000 description 2
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Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Liquid Crystal Substances (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH110279 | 1979-02-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55104270A JPS55104270A (en) | 1980-08-09 |
| JPH0465068B2 true JPH0465068B2 (enrdf_load_stackoverflow) | 1992-10-16 |
Family
ID=4202517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1160480A Granted JPS55104270A (en) | 1979-02-05 | 1980-02-04 | Novel pyrimidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55104270A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH652400A5 (en) * | 1979-11-14 | 1985-11-15 | Hoffmann La Roche | Phenyldioxanes, and liquid-crystalline mixtures containing them |
| JPS58121225A (ja) * | 1982-01-04 | 1983-07-19 | メルク・パテント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | ネマチツク相を有する異方性化合物及び該化合物を含有する液晶混合物 |
| WO2017065226A1 (ja) * | 2015-10-14 | 2017-04-20 | 日産化学工業株式会社 | 液晶配向剤、液晶配向膜、及び液晶表示素子 |
-
1980
- 1980-02-04 JP JP1160480A patent/JPS55104270A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55104270A (en) | 1980-08-09 |
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