SU332625A1 - - Google Patents
Info
- Publication number
- SU332625A1 SU332625A1 SU1262629A SU1262629A SU332625A1 SU 332625 A1 SU332625 A1 SU 332625A1 SU 1262629 A SU1262629 A SU 1262629A SU 1262629 A SU1262629 A SU 1262629A SU 332625 A1 SU332625 A1 SU 332625A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carboxylic acid
- methyl
- hydrochloride
- benzofuran
- acid
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- -1 heterocyclic carboxylic acids Chemical class 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 9
- 229930040373 Paraformaldehyde Natural products 0.000 description 8
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 8
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 8
- 229920002866 paraformaldehyde Polymers 0.000 description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IIYDTSAAECYHAE-UHFFFAOYSA-N 2-methylidenebutanoyl chloride Chemical compound CCC(=C)C(Cl)=O IIYDTSAAECYHAE-UHFFFAOYSA-N 0.000 description 1
- UVSVGUUGGNXFCD-UHFFFAOYSA-N 3,4-dichloro-5-(2-methylidenebutanoyl)-1H-indole-2-carboxylic acid Chemical compound ClC1=C(NC2=CC=C(C(=C12)Cl)C(C(CC)=C)=O)C(=O)O UVSVGUUGGNXFCD-UHFFFAOYSA-N 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical group COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- VXZHQADIRFFCMJ-UHFFFAOYSA-N 4-chloro-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1Cl VXZHQADIRFFCMJ-UHFFFAOYSA-N 0.000 description 1
- IPBNJWPJVRBOCK-UHFFFAOYSA-N 4-methyl-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C=CC2=C1C=C(O2)C(=O)O)C(C(CC)=C)=O IPBNJWPJVRBOCK-UHFFFAOYSA-N 0.000 description 1
- UWWHJLKVWYOXKR-UHFFFAOYSA-N 5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound C=C(C(=O)C=1C=CC2=C(C=C(O2)C(=O)O)C1)CC UWWHJLKVWYOXKR-UHFFFAOYSA-N 0.000 description 1
- FGDDXPCJZXDRKD-UHFFFAOYSA-N 5-[2-[(dimethylamino)methyl]butanoyl]-1-benzofuran-2-carboxylic acid hydrochloride Chemical compound Cl.CN(C)CC(C(=O)C=1C=CC2=C(C=C(O2)C(=O)O)C1)CC FGDDXPCJZXDRKD-UHFFFAOYSA-N 0.000 description 1
- ZNCWIQRZAFXNOO-UHFFFAOYSA-N 5-[2-[(dimethylamino)methyl]butanoyl]-6-methyl-1-benzofuran-2-carboxylic acid;hydrochloride Chemical group Cl.C1=C(C)C(C(=O)C(CN(C)C)CC)=CC2=C1OC(C(O)=O)=C2 ZNCWIQRZAFXNOO-UHFFFAOYSA-N 0.000 description 1
- BOQYRMQKAHZRQI-UHFFFAOYSA-N 5-[3-(dimethylamino)-2-methylpropanoyl]-6-methyl-1-benzofuran-2-carboxylic acid Chemical compound CN(C)CC(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)C)C BOQYRMQKAHZRQI-UHFFFAOYSA-N 0.000 description 1
- HILLAFZODPUECD-UHFFFAOYSA-N 5-butanoyl-1-benzofuran-2-carboxylic acid Chemical compound C(CCC)(=O)C=1C=CC2=C(C=C(O2)C(=O)O)C1 HILLAFZODPUECD-UHFFFAOYSA-N 0.000 description 1
- YVGFVSXINRSZBX-UHFFFAOYSA-N 5-butanoyl-3,4-dichloro-1-methylindole-2-carboxylic acid Chemical compound CN1C(=C(C2=C(C(=CC=C12)C(CCC)=O)Cl)Cl)C(=O)O YVGFVSXINRSZBX-UHFFFAOYSA-N 0.000 description 1
- MXMSAXLUMANTAH-UHFFFAOYSA-N 5-butanoyl-3,4-dichloro-1H-indole-2-carboxylic acid Chemical compound ClC1=C(NC2=CC=C(C(=C12)Cl)C(CCC)=O)C(=O)O MXMSAXLUMANTAH-UHFFFAOYSA-N 0.000 description 1
- YCBKOVFRLFDVSK-UHFFFAOYSA-N 5-butanoyl-4,6-dimethyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C(=CC2=C1C=C(O2)C(=O)O)C)C(CCC)=O YCBKOVFRLFDVSK-UHFFFAOYSA-N 0.000 description 1
- YAAUEYJXFCKWOP-UHFFFAOYSA-N 5-butanoyl-4-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C=CC2=C1C=C(O2)C(=O)O)C(CCC)=O YAAUEYJXFCKWOP-UHFFFAOYSA-N 0.000 description 1
- ISHJFUWRRWBXGC-UHFFFAOYSA-N 5-butanoyl-6-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC2=C(C=C(O2)C(=O)O)C=C1C(CCC)=O ISHJFUWRRWBXGC-UHFFFAOYSA-N 0.000 description 1
- PAOSYJAWQPYGKA-UHFFFAOYSA-N 6-methyl-5-pentanoyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC2=C(C=C(O2)C(=O)O)C=C1C(CCCC)=O PAOSYJAWQPYGKA-UHFFFAOYSA-N 0.000 description 1
- BDYQLWXMEDHFKC-UHFFFAOYSA-N 6-methyl-5-propanoyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC2=C(C=C(O2)C(=O)O)C=C1C(CC)=O BDYQLWXMEDHFKC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- DLTWLXUYSLIIQN-UHFFFAOYSA-N furacrinic acid Chemical compound C1=C(C)C(C(=O)C(=C)CC)=CC2=C1OC(C(O)=O)=C2 DLTWLXUYSLIIQN-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1398991A SU399107A3 (enExample) | 1968-07-26 | 1968-07-26 | |
| SU1396606A SU399106A3 (enExample) | 1968-07-26 | 1968-07-26 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SU332625A1 true SU332625A1 (enExample) | |
| SU399106A1 SU399106A1 (ru) | |
| SU399107A1 SU399107A1 (enExample) |
Family
ID=
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