JPH0430936B2 - - Google Patents
Info
- Publication number
- JPH0430936B2 JPH0430936B2 JP18269684A JP18269684A JPH0430936B2 JP H0430936 B2 JPH0430936 B2 JP H0430936B2 JP 18269684 A JP18269684 A JP 18269684A JP 18269684 A JP18269684 A JP 18269684A JP H0430936 B2 JPH0430936 B2 JP H0430936B2
- Authority
- JP
- Japan
- Prior art keywords
- tert
- butyl
- chlorophenyl
- value
- elemental analysis
- 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
- FJXLTFRZZPRENC-UHFFFAOYSA-N 3-tert-butyl-4-chlorophenol Chemical compound CC(C)(C)C1=CC(O)=CC=C1Cl FJXLTFRZZPRENC-UHFFFAOYSA-N 0.000 claims description 19
- CYEKUDPFXBLGHH-UHFFFAOYSA-N 3-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1 CYEKUDPFXBLGHH-UHFFFAOYSA-N 0.000 claims description 10
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 238000000921 elemental analysis Methods 0.000 description 23
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- 238000003756 stirring Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- -1 boric acid ester Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- JLIRZHKHGFJBGU-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) carbonochloridate Chemical compound CC(C)(C)C1=CC(OC(Cl)=O)=CC=C1Cl JLIRZHKHGFJBGU-UHFFFAOYSA-N 0.000 description 1
- XECOMKFEKSDMLR-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-(2-fluorophenyl)-n-methylcarbamate Chemical compound C=1C=CC=C(F)C=1N(C)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 XECOMKFEKSDMLR-UHFFFAOYSA-N 0.000 description 1
- DZTCDNUUYKRZRG-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-(3,4-dimethylphenyl)-n-methylcarbamate Chemical compound C=1C=C(C)C(C)=CC=1N(C)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 DZTCDNUUYKRZRG-UHFFFAOYSA-N 0.000 description 1
- HKFMEASHXHLLFT-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-(3,5-dimethylphenyl)-n-methylcarbamate Chemical compound C=1C(C)=CC(C)=CC=1N(C)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 HKFMEASHXHLLFT-UHFFFAOYSA-N 0.000 description 1
- KIOOWCIXEDVJOV-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-(3-bromophenyl)-n-methylcarbamate Chemical compound C=1C=CC(Br)=CC=1N(C)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 KIOOWCIXEDVJOV-UHFFFAOYSA-N 0.000 description 1
- YFBUYPXBWIOAPB-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-(3-chloro-4-methylphenyl)-n-methylcarbamate Chemical compound C=1C=C(C)C(Cl)=CC=1N(C)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 YFBUYPXBWIOAPB-UHFFFAOYSA-N 0.000 description 1
- FVKJYUKNPNEPJA-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-(3-chlorophenyl)-n-methylcarbamate Chemical compound C=1C=CC(Cl)=CC=1N(C)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 FVKJYUKNPNEPJA-UHFFFAOYSA-N 0.000 description 1
- DTPKJWZKCDIDEM-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-(3-fluorophenyl)-n-methylcarbamate Chemical compound C=1C=CC(F)=CC=1N(C)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 DTPKJWZKCDIDEM-UHFFFAOYSA-N 0.000 description 1
- PTHLEWFUHJQZGF-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-(3-methoxyphenyl)-n-methylcarbamate Chemical compound COC1=CC=CC(N(C)C(=O)OC=2C=C(C(Cl)=CC=2)C(C)(C)C)=C1 PTHLEWFUHJQZGF-UHFFFAOYSA-N 0.000 description 1
- YFRIZWCIMZXOJI-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-(4-fluorophenyl)-n-methylcarbamate Chemical compound C=1C=C(F)C=CC=1N(C)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 YFRIZWCIMZXOJI-UHFFFAOYSA-N 0.000 description 1
- KKNFGQWHQOKDAS-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-(6-methoxypyridin-2-yl)-n-methylcarbamate Chemical compound COC1=CC=CC(N(C)C(=O)OC=2C=C(C(Cl)=CC=2)C(C)(C)C)=N1 KKNFGQWHQOKDAS-UHFFFAOYSA-N 0.000 description 1
- IUIPXEFMXNMQSF-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-ethyl-n-(3-methylphenyl)carbamate Chemical compound C=1C=CC(C)=CC=1N(CC)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 IUIPXEFMXNMQSF-UHFFFAOYSA-N 0.000 description 1
- AJFWMZWOBRKRLF-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-methyl-n-(2-methylphenyl)carbamate Chemical compound C=1C=CC=C(C)C=1N(C)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 AJFWMZWOBRKRLF-UHFFFAOYSA-N 0.000 description 1
- ZXGMWOXRDDBYIF-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-methyl-n-(3-methylphenyl)carbamate Chemical compound C=1C=CC(C)=CC=1N(C)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 ZXGMWOXRDDBYIF-UHFFFAOYSA-N 0.000 description 1
- LTASGSJTJMEOOJ-UHFFFAOYSA-N (3-tert-butyl-4-chlorophenyl) n-methyl-n-(4-methylphenyl)carbamate Chemical compound C=1C=C(C)C=CC=1N(C)C(=O)OC1=CC=C(Cl)C(C(C)(C)C)=C1 LTASGSJTJMEOOJ-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- YLSXYZWJAZVUBD-UHFFFAOYSA-N 2-tert-butyl-4-chlorophenol Chemical compound CC(C)(C)C1=CC(Cl)=CC=C1O YLSXYZWJAZVUBD-UHFFFAOYSA-N 0.000 description 1
- VLWRKVBQUANIGI-UHFFFAOYSA-N 4-fluoro-n-methylaniline Chemical compound CNC1=CC=C(F)C=C1 VLWRKVBQUANIGI-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229940063656 aluminum chloride Drugs 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940032296 ferric chloride Drugs 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- MQTLFKGDEOQCQK-UHFFFAOYSA-N n-(3-chlorophenyl)-n-methylcarbamoyl chloride Chemical compound ClC(=O)N(C)C1=CC=CC(Cl)=C1 MQTLFKGDEOQCQK-UHFFFAOYSA-N 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- MXUJHPGODBITSO-UHFFFAOYSA-N o-(3-tert-butyl-4-chlorophenyl) chloromethanethioate Chemical compound CC(C)(C)C1=CC(OC(Cl)=S)=CC=C1Cl MXUJHPGODBITSO-UHFFFAOYSA-N 0.000 description 1
- OFOORFFHBOXYNN-UHFFFAOYSA-N o-(3-tert-butyl-4-chlorophenyl) n-(6-methoxypyridin-2-yl)-n-methylcarbamothioate Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C(Cl)=CC=2)C(C)(C)C)=N1 OFOORFFHBOXYNN-UHFFFAOYSA-N 0.000 description 1
- ULNIASHCSPJIMN-UHFFFAOYSA-N o-(3-tert-butyl-4-chlorophenyl) n-methyl-n-(3-methylphenyl)carbamothioate Chemical compound C=1C=CC(C)=CC=1N(C)C(=S)OC1=CC=C(Cl)C(C(C)(C)C)=C1 ULNIASHCSPJIMN-UHFFFAOYSA-N 0.000 description 1
- HPAMYBYDUSWUGJ-UHFFFAOYSA-N o-(3-tert-butyl-4-chlorophenyl) n-methyl-n-phenylcarbamothioate Chemical compound C=1C=CC=CC=1N(C)C(=S)OC1=CC=C(Cl)C(C(C)(C)C)=C1 HPAMYBYDUSWUGJ-UHFFFAOYSA-N 0.000 description 1
- BMBJSXKEXRFGAV-UHFFFAOYSA-N phenylcarbamothioic s-acid Chemical compound SC(=O)NC1=CC=CC=C1 BMBJSXKEXRFGAV-UHFFFAOYSA-N 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance Substances 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
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229960001939 zinc chloride Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18269684A JPS6160627A (ja) | 1984-09-03 | 1984-09-03 | ３−ｔｅｒｔ−ブチル−４−クロロフェノ−ル |
| EP85111050A EP0173993A1 (en) | 1984-09-03 | 1985-09-02 | Tert-butyl-halophenol |
| US06/840,488 US4668831A (en) | 1984-09-03 | 1986-03-14 | Tert-Butyl-halophenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18269684A JPS6160627A (ja) | 1984-09-03 | 1984-09-03 | ３−ｔｅｒｔ−ブチル−４−クロロフェノ−ル |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6160627A JPS6160627A (ja) | 1986-03-28 |
| JPH0430936B2 true JPH0430936B2 (enrdf_load_stackoverflow) | 1992-05-25 |
Family
ID=16122830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18269684A Granted JPS6160627A (ja) | 1984-09-03 | 1984-09-03 | ３−ｔｅｒｔ−ブチル−４−クロロフェノ−ル |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6160627A (enrdf_load_stackoverflow) |
-
1984
- 1984-09-03 JP JP18269684A patent/JPS6160627A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6160627A (ja) | 1986-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |