JPH045013B2 - - Google Patents
Info
- Publication number
- JPH045013B2 JPH045013B2 JP934884A JP934884A JPH045013B2 JP H045013 B2 JPH045013 B2 JP H045013B2 JP 934884 A JP934884 A JP 934884A JP 934884 A JP934884 A JP 934884A JP H045013 B2 JPH045013 B2 JP H045013B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- acetylamino
- fluoro
- formula
- general formula
- 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
- 239000000203 mixture Substances 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- IXOFPUCWZCAFJX-UHFFFAOYSA-N 2-phenylethanethioic s-acid Chemical compound SC(=O)CC1=CC=CC=C1 IXOFPUCWZCAFJX-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 150000001879 copper Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- HUPFFHLRZXIFMI-UHFFFAOYSA-N 2-amino-2-phenylethanethioic s-acid Chemical compound OC(=S)C(N)C1=CC=CC=C1 HUPFFHLRZXIFMI-UHFFFAOYSA-N 0.000 description 3
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- -1 (N-acetylamino)-1-chloro-5-fluoro-2-nitrobenzene Chemical compound 0.000 description 2
- AFJWMGOTLUUGHF-UHFFFAOYSA-N 4,5,6,7-tetrahydroisoindole-1,3-dione Chemical class C1CCCC2=C1C(=O)NC2=O AFJWMGOTLUUGHF-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940116318 copper carbonate Drugs 0.000 description 2
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 229940057995 liquid paraffin Drugs 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VZHJIJZEOCBKRA-UHFFFAOYSA-N 1-chloro-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1 VZHJIJZEOCBKRA-UHFFFAOYSA-N 0.000 description 1
- RUIXOZUENDLCST-UHFFFAOYSA-N 2-(5-acetamido-2-bromo-4-fluorophenyl)ethanethioic s-acid Chemical compound CC(=O)NC1=CC(CC(O)=S)=C(Br)C=C1F RUIXOZUENDLCST-UHFFFAOYSA-N 0.000 description 1
- IWPFJTBABFUIMF-UHFFFAOYSA-N 2-(5-amino-2-bromo-4-fluorophenyl)ethanethioic s-acid Chemical compound NC1=CC(CC(O)=S)=C(Br)C=C1F IWPFJTBABFUIMF-UHFFFAOYSA-N 0.000 description 1
- ZRPLXMHGCDGAQM-UHFFFAOYSA-N 2-(5-amino-2-chloro-4-fluorophenyl)ethanethioic s-acid Chemical compound NC1=CC(CC(O)=S)=C(Cl)C=C1F ZRPLXMHGCDGAQM-UHFFFAOYSA-N 0.000 description 1
- TWICXRHICJCOGF-UHFFFAOYSA-N 2-[3-chloro-4-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-5-fluorothiophen-2-yl]acetic acid Chemical compound ClC1=C(CC(=O)O)SC(F)=C1N1C(=O)C(CCCC2)=C2C1=O TWICXRHICJCOGF-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000000850 deacetylating effect Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- HNCIFIQHBRCORZ-UHFFFAOYSA-N n-(4-bromo-2-fluoro-5-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC([N+]([O-])=O)=C(Br)C=C1F HNCIFIQHBRCORZ-UHFFFAOYSA-N 0.000 description 1
- QXPWQNJSUGIFPM-UHFFFAOYSA-N n-(4-chloro-2-fluoro-5-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC([N+]([O-])=O)=C(Cl)C=C1F QXPWQNJSUGIFPM-UHFFFAOYSA-N 0.000 description 1
- GVRKNSAEOVXHOS-UHFFFAOYSA-N n-(4-chloro-2-fluorophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(Cl)C=C1F GVRKNSAEOVXHOS-UHFFFAOYSA-N 0.000 description 1
- ZIABKTZYXSSVSX-UHFFFAOYSA-N n-(5-amino-4-bromo-2-fluorophenyl)acetamide Chemical compound CC(=O)NC1=CC(N)=C(Br)C=C1F ZIABKTZYXSSVSX-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP934884A JPS60152453A (ja) | 1984-01-20 | 1984-01-20 | ４−（ν−アセチルアミノ）−５−フルオロ−１−ハロ−２−ニトロベンゼンおよびその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP934884A JPS60152453A (ja) | 1984-01-20 | 1984-01-20 | ４−（ν−アセチルアミノ）−５−フルオロ−１−ハロ−２−ニトロベンゼンおよびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60152453A JPS60152453A (ja) | 1985-08-10 |
| JPH045013B2 true JPH045013B2 (enrdf_load_html_response) | 1992-01-30 |
Family
ID=11717964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP934884A Granted JPS60152453A (ja) | 1984-01-20 | 1984-01-20 | ４−（ν−アセチルアミノ）−５−フルオロ−１−ハロ−２−ニトロベンゼンおよびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60152453A (enrdf_load_html_response) |
-
1984
- 1984-01-20 JP JP934884A patent/JPS60152453A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60152453A (ja) | 1985-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5066810A (en) | 3,5-dimethyl-4-methoxypyridine derivatives | |
| ZA200101507B (en) | Method for producing ortho-alkylated benzoic acid derivatives. | |
| US4324899A (en) | 2-Amino-5-cyanothiazoles and their preparation | |
| JPH06329647A (ja) | ２−（４−アルコキシ−３−シアノフェニル）チアゾール誘導体の製造法およびその新規製造中間体 | |
| US4978773A (en) | Process for the preparation of 2,6-dichlorodiphenylaminoacetic acid derivatives | |
| US4634769A (en) | Process for the preparation of 8-halo-5,6-dialkoxyquinazoline-2,4-diones and their salts | |
| JPH045013B2 (enrdf_load_html_response) | ||
| EP0036636A1 (en) | A method and intermediates for preparing 3,3'-azo-bis-(6-hydroxy benzoic acid) | |
| US4313000A (en) | Process for preparing 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro-N-alkanesulphonyl benzamides from a toluene derivative and intermediates | |
| US4894457A (en) | 7-bromo-beta-carboline compound and method for producing same | |
| CN116082181A (zh) | 一种制备3-氨基-5-乙氧基-苯甲酸的方法 | |
| US4216340A (en) | Preparation of 5-(2,4-difluorophenyl)salicylic acid and derivatives | |
| RU2103275C1 (ru) | Производные 17-галоген-4-азаандростена | |
| JPH0751561B2 (ja) | 置換フェニルチオ酢酸 | |
| JPS60248663A (ja) | アミノフエニルチオ酢酸類およびその製造法 | |
| JP2531461B2 (ja) | アミノフェニルチオ酢酸類 | |
| JP3982645B2 (ja) | Ｎ−置換ジオキソチアゾリジルベンズアミド誘導体の製造中間体 | |
| JP2531460B2 (ja) | アニリン誘導体 | |
| JP2536756B2 (ja) | ５−アルコキシアントラニル酸エステル | |
| JPS61152656A (ja) | ピペラジン誘導体 | |
| JPH06228103A (ja) | 新規なオクタヒドロアクリジン誘導体とその製造方法 | |
| JP2007522206A (ja) | 置換ベンゾピラン化合物の製造方法 | |
| JP2546850B2 (ja) | シクロプロピルメトキシ−２−メルカプトベンズイミダゾ−ル及びその製造法 | |
| JPH0317075A (ja) | ６―フルオロクロモン―２―カルボン酸誘導体の製造法 | |
| FR2684377A1 (fr) | Derives de benzoxazole et de benzothiazole leur preparation et leur utilisation comme intermediaires de synthese. |