CA1110385A - Esters polymeres actives de 3,4-di-hydroxy-2,5- diphenyl-thiophene-1,1-di-oxyde - Google Patents

Esters polymeres actives de 3,4-di-hydroxy-2,5- diphenyl-thiophene-1,1-di-oxyde

Info

Publication number: CA1110385A
Authority: CA; Canada
Prior art keywords: dioxide; yield; diphenylthiophene; solution; added
Prior art date: 1976-06-05
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

Application number

CA359,156A

Other languages

English (en)

Inventor

Wolfgang Steglich

Oswald Hollitzer

Alfred Seewald

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1976-06-05

Filing date

1980-08-27

Publication date

1981-10-06

1976-06-05 Priority claimed from DE2625539A external-priority patent/DE2625539C2/de

1980-08-27 Application filed by BASF SE filed Critical BASF SE

1980-08-27 Priority to CA359,156A priority Critical patent/CA1110385A/fr

1981-10-06 Application granted granted Critical

1981-10-06 Publication of CA1110385A publication Critical patent/CA1110385A/fr

Status Expired legal-status Critical Current

Links

150000002148 esters Chemical class 0.000 title claims abstract description 41
NPEHMGPRNCQEOS-UHFFFAOYSA-N 1,1-dioxo-2,5-diphenylthiophene-3,4-diol Chemical compound O=S1(=O)C(C=2C=CC=CC=2)=C(O)C(O)=C1C1=CC=CC=C1 NPEHMGPRNCQEOS-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 35
229920000642 polymer Polymers 0.000 claims abstract description 7
229910052799 carbon Inorganic materials 0.000 claims abstract description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-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
229920001577 copolymer Polymers 0.000 claims description 2
UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical compound O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 0.000 claims 2
WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 abstract description 13
230000009257 reactivity Effects 0.000 abstract description 4
150000003839 salts Chemical class 0.000 abstract description 3
239000000243 solution Substances 0.000 description 76
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 74
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 55
238000002844 melting Methods 0.000 description 50
230000008018 melting Effects 0.000 description 50
238000006243 chemical reaction Methods 0.000 description 44
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
239000000203 mixture Substances 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
229920005989 resin Polymers 0.000 description 33
239000011347 resin Substances 0.000 description 33
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 30
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
229940093499 ethyl acetate Drugs 0.000 description 25
238000010992 reflux Methods 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
235000019439 ethyl acetate Nutrition 0.000 description 24
-1 cyclopentad-ienone compound Chemical class 0.000 description 23
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 18
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 17
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
238000009835 boiling Methods 0.000 description 15
239000002904 solvent Substances 0.000 description 14
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
239000002253 acid Substances 0.000 description 11
238000001953 recrystallisation Methods 0.000 description 11
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
238000000034 method Methods 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
CANZBRDGRHNSGZ-NSHDSACASA-N (2s)-3-methyl-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 CANZBRDGRHNSGZ-NSHDSACASA-N 0.000 description 8
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
108090000765 processed proteins & peptides Proteins 0.000 description 8
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 8
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
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 description 6
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 6
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
235000013877 carbamide Nutrition 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
230000008030 elimination Effects 0.000 description 6
238000003379 elimination reaction Methods 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
125000002252 acyl group Chemical group 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
239000004202 carbamide Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
229960004295 valine Drugs 0.000 description 5
YBFHILNBYXCJKD-UHFFFAOYSA-N 1-(6-methylpyridin-3-yl)-2-(4-methylsulfonylphenyl)ethanone Chemical compound C1=NC(C)=CC=C1C(=O)CC1=CC=C(S(C)(=O)=O)C=C1 YBFHILNBYXCJKD-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
229940022663 acetate Drugs 0.000 description 4
239000002585 base Substances 0.000 description 4
UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 4
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
229960005190 phenylalanine Drugs 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
102000004196 processed proteins & peptides Human genes 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
150000003672 ureas Chemical class 0.000 description 4
239000004474 valine Substances 0.000 description 4
SZXBQTSZISFIAO-ZETCQYMHSA-N (2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OC(C)(C)C SZXBQTSZISFIAO-ZETCQYMHSA-N 0.000 description 3
RZFOAVRHEGQZRV-UHFFFAOYSA-N 2,3-diphenylthiophene Chemical compound S1C=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RZFOAVRHEGQZRV-UHFFFAOYSA-N 0.000 description 3
QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
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 3
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 3
KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229940024606 amino acid Drugs 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
230000008901 benefit Effects 0.000 description 3
235000019445 benzyl alcohol Nutrition 0.000 description 3
239000004305 biphenyl Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
DWKPPFQULDPWHX-VKHMYHEASA-N l-alanyl ester Chemical group COC(=O)[C@H](C)N DWKPPFQULDPWHX-VKHMYHEASA-N 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
150000003457 sulfones Chemical class 0.000 description 3
238000006276 transfer reaction Methods 0.000 description 3
ZYJPUMXJBDHSIF-NSHDSACASA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 ZYJPUMXJBDHSIF-NSHDSACASA-N 0.000 description 2
VMMKOEZGYYQVGX-UHFFFAOYSA-N 1,1-dioxo-2,5-diphenylthiophen-3-ol Chemical compound O=S1(=O)C(C=2C=CC=CC=2)=CC(O)=C1C1=CC=CC=C1 VMMKOEZGYYQVGX-UHFFFAOYSA-N 0.000 description 2
GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
RTTPRNXQDFCDIY-UHFFFAOYSA-N 2-(dibenzylamino)-2-oxoacetic acid Chemical compound C=1C=CC=CC=1CN(C(=O)C(=O)O)CC1=CC=CC=C1 RTTPRNXQDFCDIY-UHFFFAOYSA-N 0.000 description 2
HBAHZZVIEFRTEY-UHFFFAOYSA-N 2-heptylcyclohex-2-en-1-one Chemical compound CCCCCCCC1=CCCCC1=O HBAHZZVIEFRTEY-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 2
108010016626 Dipeptides Proteins 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
229920001367 Merrifield resin Polymers 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
WTINJQXJTHUFRF-YULYYXEXSA-N antamanide Chemical compound C([C@@H]1C(=O)N[C@H](C(N2CCC[C@H]2C(=O)N2CCC[C@H]2C(=O)N[C@@H](C)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N1)=O)C(C)C)C1=CC=CC=C1 WTINJQXJTHUFRF-YULYYXEXSA-N 0.000 description 2
108010036237 antamanide Proteins 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000005676 cyclic carbonates Chemical class 0.000 description 2
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
KUGLDBMQKZTXPW-JEDNCBNOSA-N methyl (2s)-2-amino-3-methylbutanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)C(C)C KUGLDBMQKZTXPW-JEDNCBNOSA-N 0.000 description 2
VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
230000008569 process Effects 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
230000036647 reaction Effects 0.000 description 2
238000012552 review Methods 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
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239000012071 phase Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
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229920006395 saturated elastomer Polymers 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
RJBVJBGFJIHJSZ-ZETCQYMHSA-N tert-butyl (2s)-2-amino-3-methylbutanoate Chemical compound CC(C)[C@H](N)C(=O)OC(C)(C)C RJBVJBGFJIHJSZ-ZETCQYMHSA-N 0.000 description 1
229940015849 thiophene Drugs 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA359,156A 1976-06-05 1980-08-27 Esters polymeres actives de 3,4-di-hydroxy-2,5- diphenyl-thiophene-1,1-di-oxyde Expired CA1110385A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA359,156A CA1110385A (fr)	1976-06-05	1980-08-27	Esters polymeres actives de 3,4-di-hydroxy-2,5- diphenyl-thiophene-1,1-di-oxyde

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE2625539A DE2625539C2 (de)	1976-06-05	1976-06-05	Cyclische Ester des 3,4-Dihydroxy-2,5-diphenyl-thiophen-1,1-dioxids und des 3,4-Dihydroxy-2,5-diphenyl-cyclopentadienons und deren Verwendung
DEP2625539.0		1976-06-05
CA279,418A CA1106388A (fr)	1976-06-05	1977-05-30	Esters cycliques de composes de dioxydes 1,1 de 3,4- dihydroxy-thiophene et de composes de 3,4-dihydroxy- cyclopentadienone
CA359,156A CA1110385A (fr)	1976-06-05	1980-08-27	Esters polymeres actives de 3,4-di-hydroxy-2,5- diphenyl-thiophene-1,1-di-oxyde

Publications (1)

Publication Number	Publication Date
CA1110385A true CA1110385A (fr)	1981-10-06

Family

ID=27165098

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA359,156A Expired CA1110385A (fr)	1976-06-05	1980-08-27	Esters polymeres actives de 3,4-di-hydroxy-2,5- diphenyl-thiophene-1,1-di-oxyde

Country Status (1)

Country	Link
CA (1)	CA1110385A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6822384B2 (en)	2000-08-17	2004-11-23	Lumera Corporation	Design and synthesis of advanced NLO materials for electro-optic applicators

1980
- 1980-08-27 CA CA359,156A patent/CA1110385A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6822384B2 (en)	2000-08-17	2004-11-23	Lumera Corporation	Design and synthesis of advanced NLO materials for electro-optic applicators
US6864375B2 (en)	2000-08-17	2005-03-08	Lumera Corporation	Highly stable and efficient nonlinear optical chromophores for electro-optic polymers

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Date	Code	Title	Description
1998-10-06	MKEX	Expiry

Publication	Publication Date	Title
SU628812A3 (ru)	1978-10-15	Способ получени органических содинений
US3238224A (en)	1966-03-01	Production of 6, 8-dithiooctanoyl amides
US3193561A (en)	1965-07-06	Novel carbamates of 5- and 6-membered hetero-sulfur compounds and process for preparing same
Kato et al.	1982	Preparation and some reactions of bis (thioacyl) sulfides
SU906372A3 (ru)	1982-02-15	Способ получени производных мочевины
US4122090A (en)	1978-10-24	Cyclic esters of 3,4-dihydroxy-thiophene-1,1-dioxide compounds and 3,4-dihydroxy-cyclopentadienone compounds
DE69833951T2 (de)	2006-08-24	Verfahren zur herstellung von substituierten alkylaminen oder salzen davon
PL89432B1 (fr)	1976-11-30
DE3002553C2 (fr)	1988-10-27
EP0139184A1 (fr)	1985-05-02	Thioxanthénylméthyloxycarbonyl dioxydes et procédé pour la synthèse de peptides les utilisant
US4594424A (en)	1986-06-10	5-mercapto-1,2,3-thiadiazoles composition and process for preparing the same
US2785191A (en)	1957-03-12	Acylmercapto-alkylamines and process for the manufacture thereof
CA1074808A (fr)	1980-04-01	Methode pour synthetiser des esters d'acides thiocarbamiques
US3691186A (en)	1972-09-12	Certain substituted benzthiazole-n-oxides and their preparation
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