DD209443A5 - Verfahren zur herstellung von acylaminoderivaten von 1-(aryl- oder subst.-aryl)amino-1-thioalkancarboxysaeuren - Google Patents
Verfahren zur herstellung von acylaminoderivaten von 1-(aryl- oder subst.-aryl)amino-1-thioalkancarboxysaeuren Download PDFInfo
- Publication number
- DD209443A5 DD209443A5 DD81244217A DD24421781A DD209443A5 DD 209443 A5 DD209443 A5 DD 209443A5 DD 81244217 A DD81244217 A DD 81244217A DD 24421781 A DD24421781 A DD 24421781A DD 209443 A5 DD209443 A5 DD 209443A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- lower alkyl
- aryl
- formula
- tert
- bromine
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 150000001266 acyl halides Chemical class 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- -1 chloro, bromo, iodo Chemical group 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000000460 chlorine Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 239000011630 iodine Chemical group 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- 150000001768 cations Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 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 description 2
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical group BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 15
- 125000004442 acylamino group Chemical group 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 2
- 239000000417 fungicide Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 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 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- 150000001263 acyl chlorides Chemical class 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002516 radical scavenger Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- TUZFIWBNGKNFPW-UHFFFAOYSA-M sodium;2-methylpropane-2-thiolate Chemical compound [Na+].CC(C)(C)[S-] TUZFIWBNGKNFPW-UHFFFAOYSA-M 0.000 description 4
- 150000007944 thiolates Chemical class 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 150000003138 primary alcohols Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- ZVVWZNFSMIFGEP-UHFFFAOYSA-N 2-(4-ethoxyphenyl)acetic acid Chemical compound CCOC1=CC=C(CC(O)=O)C=C1 ZVVWZNFSMIFGEP-UHFFFAOYSA-N 0.000 description 2
- BIQVQVGFZQXERD-UHFFFAOYSA-N 3-methyloxirane-2-carbonyl chloride Chemical compound CC1OC1C(Cl)=O BIQVQVGFZQXERD-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- JVVBLWPCBNOZQC-UHFFFAOYSA-N 4-tert-butylsulfanyl-2-(2,6-dimethylanilino)butanoic acid Chemical compound C(=O)(O)C(CCSC(C)(C)C)NC1=C(C=CC=C1C)C JVVBLWPCBNOZQC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZBRWJPVULTZZCE-UHFFFAOYSA-N 1-propylsulfanylbutane Chemical class CCCCSCCC ZBRWJPVULTZZCE-UHFFFAOYSA-N 0.000 description 1
- MMEXIIGRXCODNK-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)acetic acid Chemical compound CC1=CC=CC(C)=C1CC(O)=O MMEXIIGRXCODNK-UHFFFAOYSA-N 0.000 description 1
- OYMPEYTUENTYNK-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)acetyl chloride Chemical group CC1=CC=CC(C)=C1CC(Cl)=O OYMPEYTUENTYNK-UHFFFAOYSA-N 0.000 description 1
- DOJYHQGYPJKSPT-UHFFFAOYSA-N 2-(4-ethoxyphenyl)acetyl chloride Chemical group CCOC1=CC=C(CC(Cl)=O)C=C1 DOJYHQGYPJKSPT-UHFFFAOYSA-N 0.000 description 1
- LCIMJULVQOQTEZ-UHFFFAOYSA-N 2-hydroxyacetyl chloride Chemical group OCC(Cl)=O LCIMJULVQOQTEZ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- MTVMGLPBDYLGDV-UHFFFAOYSA-N 2-methyl-2-propylsulfanylpropane Chemical compound CCCSC(C)(C)C MTVMGLPBDYLGDV-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical group ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
- UJXIOVIFPTXDHU-UHFFFAOYSA-N 2-phenylethanethioyl chloride Chemical group ClC(=S)CC1=CC=CC=C1 UJXIOVIFPTXDHU-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- SEDGGCMDYFKAQN-UHFFFAOYSA-N 3-methyloxirane-2-carboxylic acid Chemical compound CC1OC1C(O)=O SEDGGCMDYFKAQN-UHFFFAOYSA-N 0.000 description 1
- BKPXEDRKBBTGAQ-UHFFFAOYSA-N 4-(2,6-dimethylanilino)oxolan-2-one Chemical compound CC1=CC=CC(C)=C1NC1CC(=O)OC1 BKPXEDRKBBTGAQ-UHFFFAOYSA-N 0.000 description 1
- YWLUWLQYBLKWCF-UHFFFAOYSA-N 4-tert-butylsulfanyl-2-(2-methoxy-6-methylanilino)butanoic acid Chemical compound C(=O)(O)C(CCSC(C)(C)C)NC1=C(C=CC=C1C)OC YWLUWLQYBLKWCF-UHFFFAOYSA-N 0.000 description 1
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OAEZDDAJJCXHAL-UHFFFAOYSA-N C(=O)(O)C1(CC=CC2=CC=CC=C12)NCCCSC(C)(C)C Chemical compound C(=O)(O)C1(CC=CC2=CC=CC=C12)NCCCSC(C)(C)C OAEZDDAJJCXHAL-UHFFFAOYSA-N 0.000 description 1
- BKUXQUDSHLIZMB-UHFFFAOYSA-N C1(=CC=CC=C1)N(C(C(Cl)Cl)=O)C(CSC(C)(C)C)CC(=O)OC(C(Cl)Cl)=O Chemical compound C1(=CC=CC=C1)N(C(C(Cl)Cl)=O)C(CSC(C)(C)C)CC(=O)OC(C(Cl)Cl)=O BKUXQUDSHLIZMB-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- DUTFXOILJRIQSW-UHFFFAOYSA-N O-hexanethioyl hexanethioate Chemical compound CCCCCC(=S)OC(=S)CCCCC DUTFXOILJRIQSW-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical group CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001262 acyl bromides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical group ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- GDAMWPQNFIQQAB-UHFFFAOYSA-M potassium;2-methylpropane-2-thiolate Chemical compound [K+].CC(C)(C)[S-] GDAMWPQNFIQQAB-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- GLBUZFYJIIWCFB-UHFFFAOYSA-N propanethioyl chloride Chemical group CCC(Cl)=S GLBUZFYJIIWCFB-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16245380A | 1980-06-23 | 1980-06-23 | |
| US06/184,846 US4311849A (en) | 1980-09-08 | 1980-09-08 | Process for making 3-(N-arylamino)-gamma-butyrothiolactones |
| US20086480A | 1980-10-27 | 1980-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD209443A5 true DD209443A5 (de) | 1984-05-09 |
Family
ID=27388753
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81244217A DD209443A5 (de) | 1980-06-23 | 1981-06-23 | Verfahren zur herstellung von acylaminoderivaten von 1-(aryl- oder subst.-aryl)amino-1-thioalkancarboxysaeuren |
| DD81244216A DD203718A5 (de) | 1980-06-23 | 1981-06-23 | Verfahren zur herstellung von 1-(aryl- oder subst.-aryl)amino-1-thioalkancarboxylsalzen bzw. den ensprechenden carboxysaeuren |
| DD81231058A DD160416A5 (de) | 1980-06-23 | 1981-06-23 | Verfahren zur herstellung von 3-(n-aryl-n-acylamio)-gamma-butyrothiolactonen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81244216A DD203718A5 (de) | 1980-06-23 | 1981-06-23 | Verfahren zur herstellung von 1-(aryl- oder subst.-aryl)amino-1-thioalkancarboxylsalzen bzw. den ensprechenden carboxysaeuren |
| DD81231058A DD160416A5 (de) | 1980-06-23 | 1981-06-23 | Verfahren zur herstellung von 3-(n-aryl-n-acylamio)-gamma-butyrothiolactonen |
Country Status (8)
| Country | Link |
|---|---|
| CH (1) | CH648307A5 (enrdf_load_stackoverflow) |
| DD (3) | DD209443A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3123864A1 (enrdf_load_stackoverflow) |
| ES (3) | ES8300105A1 (enrdf_load_stackoverflow) |
| FR (3) | FR2485013A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2078741B (enrdf_load_stackoverflow) |
| IT (1) | IT1136849B (enrdf_load_stackoverflow) |
| NL (1) | NL8103024A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5175310A (en) * | 1990-03-16 | 1992-12-29 | Elf Atochem North America, Inc. | Process for producing alkylthio- and arylthio-substituted carboxylic acids and their thioesters |
| CN1035252C (zh) * | 1993-11-23 | 1997-06-25 | 王桂英 | 氨甲基甲酸-1，1，1-三氯-2-(2,4－二氯硫酚基) 乙基酯及其制备方法 |
| ES2088817B1 (es) * | 1993-12-02 | 1997-08-01 | Univ La Laguna | Control de nematodos fitoparasitos con lignanos tipo dibencil-butirolactonas. |
| CN114891221B (zh) * | 2019-10-14 | 2023-09-15 | 中国科学院上海有机化学研究所 | 聚（γ-硫代丁内酯） |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2408601A1 (fr) * | 1977-11-01 | 1979-06-08 | Chevron Res | Procede d'acylation d'une aniline substituee par une lactone en l'absence d'accepteur d'acide |
| BR8000986A (pt) * | 1979-02-22 | 1980-10-29 | Chevron Res | Composto fungicida, processo para controlar o crescimento de fungos, composicao fungicidas e processo para o controle de fungos |
| MA19111A1 (fr) * | 1979-10-26 | 1981-12-31 | Ciba Geigy Ag | Derives de l'homoserine,procede pour leur preparation et leur utilisation en tant que microbicides |
-
1981
- 1981-06-16 DE DE19813123864 patent/DE3123864A1/de not_active Withdrawn
- 1981-06-19 FR FR8112167A patent/FR2485013A1/fr active Granted
- 1981-06-22 IT IT22482/81A patent/IT1136849B/it active
- 1981-06-23 DD DD81244217A patent/DD209443A5/de unknown
- 1981-06-23 GB GB8119334A patent/GB2078741B/en not_active Expired
- 1981-06-23 CH CH4154/81A patent/CH648307A5/de not_active IP Right Cessation
- 1981-06-23 DD DD81244216A patent/DD203718A5/de unknown
- 1981-06-23 NL NL8103024A patent/NL8103024A/nl not_active Application Discontinuation
- 1981-06-23 DD DD81231058A patent/DD160416A5/de unknown
- 1981-06-23 ES ES503313A patent/ES8300105A1/es not_active Expired
- 1981-11-17 FR FR8121478A patent/FR2491069B1/fr not_active Expired
- 1981-11-17 FR FR8121477A patent/FR2491062A1/fr active Granted
-
1982
- 1982-06-14 ES ES513070A patent/ES8304114A1/es not_active Expired
- 1982-06-14 ES ES513071A patent/ES8304115A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2491069A1 (enrdf_load_stackoverflow) | 1982-04-02 |
| FR2485013A1 (fr) | 1981-12-24 |
| FR2491062A1 (fr) | 1982-04-02 |
| FR2485013B1 (enrdf_load_stackoverflow) | 1984-06-29 |
| IT8122482A0 (it) | 1981-06-22 |
| GB2078741A (en) | 1982-01-13 |
| FR2491069B1 (enrdf_load_stackoverflow) | 1983-12-16 |
| FR2491062B1 (enrdf_load_stackoverflow) | 1985-01-18 |
| NL8103024A (nl) | 1982-01-18 |
| ES513070A0 (es) | 1983-02-16 |
| ES8304114A1 (es) | 1983-02-16 |
| CH648307A5 (de) | 1985-03-15 |
| DE3123864A1 (de) | 1982-03-04 |
| ES513071A0 (es) | 1983-02-16 |
| IT1136849B (it) | 1986-09-03 |
| ES503313A0 (es) | 1982-10-01 |
| ES8304115A1 (es) | 1983-02-16 |
| ES8300105A1 (es) | 1982-10-01 |
| DD203718A5 (de) | 1983-11-02 |
| DD160416A5 (de) | 1983-07-27 |
| GB2078741B (en) | 1984-02-08 |
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