CH621542A5 - Process for the preparation of isothioureidobenzenes - Google Patents
Process for the preparation of isothioureidobenzenes Download PDFInfo
- Publication number
- CH621542A5 CH621542A5 CH549577A CH549577A CH621542A5 CH 621542 A5 CH621542 A5 CH 621542A5 CH 549577 A CH549577 A CH 549577A CH 549577 A CH549577 A CH 549577A CH 621542 A5 CH621542 A5 CH 621542A5
- Authority
- CH
- Switzerland
- Prior art keywords
- ureido
- carbomethoxy
- alkyl
- mol
- methylisothio
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 15
- 230000008569 process Effects 0.000 title claims description 4
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical class NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 title 1
- -1 aralkyl radical Chemical class 0.000 claims description 87
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 150000003254 radicals Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 147
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 144
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 117
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 97
- 239000000203 mixture Substances 0.000 description 63
- 239000002244 precipitate Substances 0.000 description 48
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 47
- 238000000354 decomposition reaction Methods 0.000 description 47
- 238000001914 filtration Methods 0.000 description 42
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 239000007864 aqueous solution Substances 0.000 description 37
- 239000000725 suspension Substances 0.000 description 36
- SOVIIRRAYRVPQE-UHFFFAOYSA-N methyl n-[(2-amino-5-benzoylphenyl)carbamothioyl]carbamate Chemical compound C1=C(N)C(NC(=S)NC(=O)OC)=CC(C(=O)C=2C=CC=CC=2)=C1 SOVIIRRAYRVPQE-UHFFFAOYSA-N 0.000 description 26
- 238000004458 analytical method Methods 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 20
- 241001465754 Metazoa Species 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 239000012065 filter cake Substances 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- LBFAAYMITJMZOC-UHFFFAOYSA-N methyl n-(sulfanylidenemethylidene)carbamate Chemical compound COC(=O)N=C=S LBFAAYMITJMZOC-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000507 anthelmentic effect Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- RXCOGDYOZQGGMK-UHFFFAOYSA-N (3,4-diaminophenyl)-phenylmethanone Chemical compound C1=C(N)C(N)=CC=C1C(=O)C1=CC=CC=C1 RXCOGDYOZQGGMK-UHFFFAOYSA-N 0.000 description 5
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 5
- 241001494479 Pecora Species 0.000 description 5
- 239000000921 anthelmintic agent Substances 0.000 description 5
- 229940124339 anthelmintic agent Drugs 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000282414 Homo sapiens Species 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 238000003828 vacuum filtration Methods 0.000 description 4
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 3
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 3
- NDYYWMXJZWHRLZ-UHFFFAOYSA-N 2-methoxyethyl carbonochloridate Chemical compound COCCOC(Cl)=O NDYYWMXJZWHRLZ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- AQGIYEAWUUDQCN-UHFFFAOYSA-N [2-(methoxycarbonylcarbamothioylamino)-4-propylphenyl]-oxo-sulfidoazanium Chemical compound C(=O)(OC)NC(NC1=C(C=CC(=C1)CCC)[N+](=S)[O-])=S AQGIYEAWUUDQCN-UHFFFAOYSA-N 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 229940121375 antifungal agent Drugs 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- ZOPDINBAHICTGW-UHFFFAOYSA-N hexyl N-[(2-amino-5-benzoylphenyl)carbamothioyl]carbamate Chemical compound C(=O)(OCCCCCC)NC(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)=S ZOPDINBAHICTGW-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- QHGIOZSQKOCBIW-UHFFFAOYSA-N methyl N-[(2-amino-4-benzoylphenyl)carbamothioyl]carbamate Chemical compound NC1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)NC(=S)NC(OC)=O QHGIOZSQKOCBIW-UHFFFAOYSA-N 0.000 description 3
- NAJACIUCVBXOIJ-UHFFFAOYSA-N methyl N-[(4-benzoyl-2-nitrophenyl)carbamothioyl]carbamate Chemical compound COC(=O)NC(=S)NC1=C(C=C(C=C1)C(C1=CC=CC=C1)=O)[N+](=O)[O-] NAJACIUCVBXOIJ-UHFFFAOYSA-N 0.000 description 3
- WLLQBAZOQHUNBF-UHFFFAOYSA-N methyl N-[[2-amino-5-(benzenesulfonyl)phenyl]carbamothioyl]carbamate Chemical compound C(=O)(OC)NC(NC1=C(N)C=CC(=C1)S(=O)(=O)C1=CC=CC=C1)=S WLLQBAZOQHUNBF-UHFFFAOYSA-N 0.000 description 3
- DNWQLNWKXHENLO-UHFFFAOYSA-N methyl n-[(2-amino-4-butylphenyl)carbamothioyl]carbamate Chemical compound CCCCC1=CC=C(NC(=S)NC(=O)OC)C(N)=C1 DNWQLNWKXHENLO-UHFFFAOYSA-N 0.000 description 3
- QVXGXKQYZXVOJG-UHFFFAOYSA-N methyl n-[(2-amino-5-nitrophenyl)carbamothioyl]carbamate Chemical compound COC(=O)NC(=S)NC1=CC([N+]([O-])=O)=CC=C1N QVXGXKQYZXVOJG-UHFFFAOYSA-N 0.000 description 3
- OUPBBRVWQIBRIS-UHFFFAOYSA-N methyl n-[(2-amino-5-propylsulfanylphenyl)carbamothioyl]carbamate Chemical compound CCCSC1=CC=C(N)C(NC(=S)NC(=O)OC)=C1 OUPBBRVWQIBRIS-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- LSMGZIIPUAHUMX-UHFFFAOYSA-N phenyl 4-amino-3-(methoxycarbonylcarbamothioylamino)benzenesulfonate Chemical compound C(=O)(OC)NC(NC1=C(N)C=CC(=C1)S(=O)(=O)OC1=CC=CC=C1)=S LSMGZIIPUAHUMX-UHFFFAOYSA-N 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 3
- 229940116357 potassium thiocyanate Drugs 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000001119 stannous chloride Substances 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- NLCPQMUVBQILMA-UHFFFAOYSA-N 2-nitro-5-propylsulfanylaniline Chemical compound CCCSC1=CC=C([N+]([O-])=O)C(N)=C1 NLCPQMUVBQILMA-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- WQEGHHLKDKIWKM-UHFFFAOYSA-N 4-butylbenzene-1,2-diamine Chemical compound CCCCC1=CC=C(N)C(N)=C1 WQEGHHLKDKIWKM-UHFFFAOYSA-N 0.000 description 2
- VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 241000242711 Fasciola hepatica Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
- 241000282849 Ruminantia Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009418 agronomic effect Effects 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- NSKHPCZJWIBPMG-UHFFFAOYSA-N ethyl N-[(2-amino-5-benzoylphenyl)carbamothioyl]carbamate Chemical compound C(=O)(OCC)NC(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)=S NSKHPCZJWIBPMG-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- DFKNQFLAQNQXEA-UHFFFAOYSA-N methyl (nz)-n-[(2-amino-5-propylsulfanylanilino)-methylsulfanylmethylidene]carbamate Chemical compound CCCSC1=CC=C(N)C(NC(SC)=NC(=O)OC)=C1 DFKNQFLAQNQXEA-UHFFFAOYSA-N 0.000 description 2
- AJKIQBMDNWZZER-UHFFFAOYSA-N methyl N-[(2-amino-5-propylsulfonylphenyl)carbamothioyl]carbamate Chemical compound NC1=C(C=C(C=C1)S(=O)(=O)CCC)NC(=S)NC(=O)OC AJKIQBMDNWZZER-UHFFFAOYSA-N 0.000 description 2
- YTGVAKDRFRGYAM-UHFFFAOYSA-N methyl n-[(2-aminophenyl)carbamothioyl]carbamate Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1N YTGVAKDRFRGYAM-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- NGOOFAMQPUEDJM-UHFFFAOYSA-N (4-amino-3-nitrophenyl)-phenylmethanone Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1C(=O)C1=CC=CC=C1 NGOOFAMQPUEDJM-UHFFFAOYSA-N 0.000 description 1
- GKQXPTHQTXCXEV-UHFFFAOYSA-N (4-chlorophenyl)methanethiol Chemical compound SCC1=CC=C(Cl)C=C1 GKQXPTHQTXCXEV-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006531 (C2-C5) alkyl group Chemical group 0.000 description 1
- QLRBNEZOQPLERN-UHFFFAOYSA-N (sulfonylamino)benzene Chemical compound O=S(=O)=NC1=CC=CC=C1 QLRBNEZOQPLERN-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- HXBMIQJOSHZCFX-UHFFFAOYSA-N 1-(bromomethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CBr HXBMIQJOSHZCFX-UHFFFAOYSA-N 0.000 description 1
- FWLWTILKTABGKQ-UHFFFAOYSA-N 1-(bromomethyl)-3-methylbenzene Chemical compound CC1=CC=CC(CBr)=C1 FWLWTILKTABGKQ-UHFFFAOYSA-N 0.000 description 1
- WZRKSPFYXUXINF-UHFFFAOYSA-N 1-(bromomethyl)-4-methylbenzene Chemical compound CC1=CC=C(CBr)C=C1 WZRKSPFYXUXINF-UHFFFAOYSA-N 0.000 description 1
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
- ALOQTNHQNMYBDE-UHFFFAOYSA-N 1-bromo-4-methoxybutane Chemical compound COCCCCBr ALOQTNHQNMYBDE-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000000034 thioazolyl group Chemical group 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/38—Isothioureas containing any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68355476A | 1976-05-05 | 1976-05-05 | |
| US78323477A | 1977-03-31 | 1977-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621542A5 true CH621542A5 (en) | 1981-02-13 |
Family
ID=27103138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH549577A CH621542A5 (en) | 1976-05-05 | 1977-05-03 | Process for the preparation of isothioureidobenzenes |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS537645A (OSRAM) |
| AR (1) | AR213309A1 (OSRAM) |
| AU (1) | AU2493077A (OSRAM) |
| BR (1) | BR7702864A (OSRAM) |
| CA (1) | CA1105038A (OSRAM) |
| CH (1) | CH621542A5 (OSRAM) |
| DE (1) | DE2720290A1 (OSRAM) |
| DK (1) | DK193177A (OSRAM) |
| FR (1) | FR2372154A1 (OSRAM) |
| GB (1) | GB1576633A (OSRAM) |
| IL (1) | IL52004A (OSRAM) |
| NL (1) | NL7704975A (OSRAM) |
| NZ (1) | NZ183993A (OSRAM) |
| SE (1) | SE7705156L (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4348406A (en) * | 1980-10-20 | 1982-09-07 | Schering Corporation | Novel guanidine derivatives |
| IT1177379B (it) * | 1984-12-11 | 1987-08-26 | Anic Spa | Derivati della sostanza p e di suoi frammenti |
| JP5773975B2 (ja) | 2012-12-26 | 2015-09-02 | 本田技研工業株式会社 | 鞍乗り型車両の排気管カバー構造 |
-
1977
- 1977-04-29 AR AR267417A patent/AR213309A1/es active
- 1977-05-02 GB GB18212/77A patent/GB1576633A/en not_active Expired
- 1977-05-03 SE SE7705156A patent/SE7705156L/xx unknown
- 1977-05-03 DK DK193177A patent/DK193177A/da unknown
- 1977-05-03 NZ NZ183993A patent/NZ183993A/xx unknown
- 1977-05-03 CH CH549577A patent/CH621542A5/fr not_active IP Right Cessation
- 1977-05-04 CA CA277,661A patent/CA1105038A/en not_active Expired
- 1977-05-04 BR BR7702864A patent/BR7702864A/pt unknown
- 1977-05-04 IL IL52004A patent/IL52004A/xx unknown
- 1977-05-04 JP JP5166077A patent/JPS537645A/ja active Pending
- 1977-05-05 DE DE19772720290 patent/DE2720290A1/de not_active Withdrawn
- 1977-05-05 AU AU24930/77A patent/AU2493077A/en not_active Expired
- 1977-05-05 FR FR7713728A patent/FR2372154A1/fr active Granted
- 1977-05-05 NL NL7704975A patent/NL7704975A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR213309A1 (es) | 1979-01-15 |
| DK193177A (da) | 1977-11-06 |
| NL7704975A (nl) | 1977-11-08 |
| FR2372154A1 (fr) | 1978-06-23 |
| JPS537645A (en) | 1978-01-24 |
| SE7705156L (sv) | 1977-11-06 |
| GB1576633A (en) | 1980-10-08 |
| FR2372154B1 (OSRAM) | 1980-03-07 |
| NZ183993A (en) | 1979-11-01 |
| DE2720290A1 (de) | 1977-11-17 |
| BR7702864A (pt) | 1978-03-28 |
| AU2493077A (en) | 1978-11-09 |
| IL52004A (en) | 1981-05-20 |
| IL52004A0 (en) | 1977-07-31 |
| CA1105038A (en) | 1981-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |