PL67938B1

PL67938B1 -

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Publication number: PL67938B1
Authority: PL; Poland
Prior art keywords: formula; compound; acid; hydrogen; general formula
Prior art date: 1967-10-30

Application number

PL123312A

Other languages

English (en)

Polish (pl)

Original Assignee

Ciba Geigy Ag

Filing date

1967-10-30

Publication date

1972-12-30

1967-10-30 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1972-12-30 Publication of PL67938B1 publication Critical patent/PL67938B1/pl

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239000002253 acid Substances 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
-1 alkali metal salt Chemical class 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 4
PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 25
229910052739 hydrogen Inorganic materials 0.000 claims 11
239000001257 hydrogen Substances 0.000 claims 11
238000000034 method Methods 0.000 claims 11
125000000217 alkyl group Chemical group 0.000 claims 10
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 6
150000002431 hydrogen Chemical class 0.000 claims 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
150000001735 carboxylic acids Chemical class 0.000 claims 4
125000004093 cyano group Chemical group *C#N 0.000 claims 4
229910052783 alkali metal Inorganic materials 0.000 claims 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims 3
229910002092 carbon dioxide Inorganic materials 0.000 claims 3
239000001569 carbon dioxide Substances 0.000 claims 3
150000003839 salts Chemical class 0.000 claims 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
125000005907 alkyl ester group Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
150000001734 carboxylic acid salts Chemical class 0.000 claims 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
150000007529 inorganic bases Chemical class 0.000 claims 2
239000000178 monomer Substances 0.000 claims 2
150000007530 organic bases Chemical class 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
229920000642 polymer Polymers 0.000 claims 2
238000002360 preparation method Methods 0.000 claims 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims 2
125000001424 substituent group Chemical group 0.000 claims 2
229910052727 yttrium Inorganic materials 0.000 claims 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
239000004215 Carbon black (E152) Substances 0.000 claims 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
229930194542 Keto Natural products 0.000 claims 1
240000005265 Lupinus mutabilis Species 0.000 claims 1
235000008755 Lupinus mutabilis Nutrition 0.000 claims 1
235000019095 Sechium edule Nutrition 0.000 claims 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 claims 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000000304 alkynyl group Chemical group 0.000 claims 1
150000001408 amides Chemical class 0.000 claims 1
229910021529 ammonia Inorganic materials 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000002585 base Substances 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
229910002091 carbon monoxide Inorganic materials 0.000 claims 1
150000001733 carboxylic acid esters Chemical class 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
229910052801 chlorine Chemical group 0.000 claims 1
239000000460 chlorine Chemical group 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 claims 1
229910052802 copper Inorganic materials 0.000 claims 1
239000010949 copper Substances 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 1
229910052697 platinum Inorganic materials 0.000 claims 1
229920001021 polysulfide Polymers 0.000 claims 1
239000005077 polysulfide Substances 0.000 claims 1
150000008117 polysulfides Polymers 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
150000003335 secondary amines Chemical class 0.000 claims 1
229910001923 silver oxide Inorganic materials 0.000 claims 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
150000003556 thioamides Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 4
KGGLRUUIPVNGRB-UHFFFAOYSA-N ethyl 2-(4-amino-3-bromophenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(N)C(Br)=C1 KGGLRUUIPVNGRB-UHFFFAOYSA-N 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
LGUKTYAEODCQMW-UHFFFAOYSA-N 2-(4-amino-3-bromophenyl)acetic acid Chemical compound NC1=CC=C(CC(O)=O)C=C1Br LGUKTYAEODCQMW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
GGBKBLCIMQPSCO-UHFFFAOYSA-N 2-(4-acetamido-3-bromophenyl)acetic acid Chemical compound CC(=O)NC1=CC=C(CC(O)=O)C=C1Br GGBKBLCIMQPSCO-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
UCMFZAZGBPYDAD-UHFFFAOYSA-N 2-(3-chloro-4-pyrrol-1-ylphenyl)acetic acid Chemical compound ClC=1C=C(C=CC1N1C=CC=C1)CC(=O)O UCMFZAZGBPYDAD-UHFFFAOYSA-N 0.000 description 1
BOTYEUNQFXTDNF-UHFFFAOYSA-N 2-(3-chloro-4-pyrrol-1-ylphenyl)butanoic acid Chemical compound ClC=1C=C(C=CC1N1C=CC=C1)C(C(=O)O)CC BOTYEUNQFXTDNF-UHFFFAOYSA-N 0.000 description 1
ANAQSKGWPSBAPF-UHFFFAOYSA-N 2-(3-chloro-4-pyrrol-1-ylphenyl)propanoic acid Chemical compound ClC1=CC(C(C(O)=O)C)=CC=C1N1C=CC=C1 ANAQSKGWPSBAPF-UHFFFAOYSA-N 0.000 description 1
WAPLXGPARWRGJO-UHFFFAOYSA-N 2-(4-aminophenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C(N)C=C1 WAPLXGPARWRGJO-UHFFFAOYSA-N 0.000 description 1
REEGEVWKFIVCQX-UHFFFAOYSA-N 2-(4-pyrrol-1-ylphenyl)butanoic acid Chemical compound N1(C=CC=C1)C1=CC=C(C=C1)C(C(=O)O)CC REEGEVWKFIVCQX-UHFFFAOYSA-N 0.000 description 1
BWCOHXICZCDKPF-UHFFFAOYSA-N 2-(4-pyrrol-1-ylphenyl)propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1N1C=CC=C1 BWCOHXICZCDKPF-UHFFFAOYSA-N 0.000 description 1
XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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 1
239000004153 Potassium bromate Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
WYTIAWGDEWSUGP-UHFFFAOYSA-N methyl 2-(3-chloro-4-pyrrol-1-ylphenyl)propanoate Chemical compound COC(C(C)C1=CC(=C(C=C1)N1C=CC=C1)Cl)=O WYTIAWGDEWSUGP-UHFFFAOYSA-N 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229960005382 phenolphthalein Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229940094037 potassium bromate Drugs 0.000 description 1
235000019396 potassium bromate Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1

PL123312A 1967-10-30 PL67938B1 (enExample)