DE2800111A1 - Verfahren zur herstellung von aminophenylharnstoffen und aminocarbanylaten - Google Patents
Verfahren zur herstellung von aminophenylharnstoffen und aminocarbanylatenInfo
- Publication number
- DE2800111A1 DE2800111A1 DE19782800111 DE2800111A DE2800111A1 DE 2800111 A1 DE2800111 A1 DE 2800111A1 DE 19782800111 DE19782800111 DE 19782800111 DE 2800111 A DE2800111 A DE 2800111A DE 2800111 A1 DE2800111 A1 DE 2800111A1
- Authority
- DE
- Germany
- Prior art keywords
- optionally substituted
- acid
- parts
- cycloalkyl
- methyl
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 amino, hydroxyl Chemical group 0.000 claims description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 150000001555 benzenes Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 235000003891 ferrous sulphate Nutrition 0.000 claims 1
- 239000011790 ferrous sulphate Substances 0.000 claims 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims 1
- 229940116269 uric acid Drugs 0.000 claims 1
- 239000003480 eluent Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- XUFXDODGXLVPNJ-UHFFFAOYSA-N 1-ethyl-3-phenylurea Chemical compound CCNC(=O)NC1=CC=CC=C1 XUFXDODGXLVPNJ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BLSVCHHBHKGCSQ-UHFFFAOYSA-N (2-methylphenyl)urea Chemical compound CC1=CC=CC=C1NC(N)=O BLSVCHHBHKGCSQ-UHFFFAOYSA-N 0.000 description 2
- MHVJUTLRTHDAOG-UHFFFAOYSA-N (4-hydroxyphenyl)urea Chemical compound NC(=O)NC1=CC=C(O)C=C1 MHVJUTLRTHDAOG-UHFFFAOYSA-N 0.000 description 2
- PGUKYDVWVXRPKK-UHFFFAOYSA-N (4-methoxyphenyl)urea Chemical compound COC1=CC=C(NC(N)=O)C=C1 PGUKYDVWVXRPKK-UHFFFAOYSA-N 0.000 description 2
- CIQJWKNJDQKPPO-UHFFFAOYSA-N 1-chloropiperidine Chemical compound ClN1CCCCC1 CIQJWKNJDQKPPO-UHFFFAOYSA-N 0.000 description 2
- CLAMVVWEAVXTGT-UHFFFAOYSA-N 1-ethyl-3-(4-methoxyphenyl)urea Chemical compound CCNC(=O)NC1=CC=C(OC)C=C1 CLAMVVWEAVXTGT-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- GGLIEWRLXDLBBF-UHFFFAOYSA-N Dulcin Chemical compound CCOC1=CC=C(NC(N)=O)C=C1 GGLIEWRLXDLBBF-UHFFFAOYSA-N 0.000 description 2
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- ASPIQYFYSMQBHA-UHFFFAOYSA-N (2-chlorophenyl)urea Chemical compound NC(=O)NC1=CC=CC=C1Cl ASPIQYFYSMQBHA-UHFFFAOYSA-N 0.000 description 1
- QUAYEHVOVRZTOO-UHFFFAOYSA-N (2-cyanophenyl)urea Chemical compound NC(=O)NC1=CC=CC=C1C#N QUAYEHVOVRZTOO-UHFFFAOYSA-N 0.000 description 1
- BQJBONTVMVGWPV-UHFFFAOYSA-N (2-hydroxyphenyl)urea Chemical compound NC(=O)NC1=CC=CC=C1O BQJBONTVMVGWPV-UHFFFAOYSA-N 0.000 description 1
- UXDXYHPPJXGOTF-UHFFFAOYSA-N (2-iodophenyl)urea Chemical compound NC(=O)NC1=CC=CC=C1I UXDXYHPPJXGOTF-UHFFFAOYSA-N 0.000 description 1
- IABLBGQNBFMFFZ-UHFFFAOYSA-N (2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(N)=O IABLBGQNBFMFFZ-UHFFFAOYSA-N 0.000 description 1
- OEZUXIKLRGSNBT-UHFFFAOYSA-N (2-nitrophenyl)urea Chemical compound NC(=O)NC1=CC=CC=C1[N+]([O-])=O OEZUXIKLRGSNBT-UHFFFAOYSA-N 0.000 description 1
- JWZQSHIHUFFPHV-UHFFFAOYSA-N (2-propan-2-ylphenyl)urea Chemical compound CC(C)C1=CC=CC=C1NC(N)=O JWZQSHIHUFFPHV-UHFFFAOYSA-N 0.000 description 1
- ABECWVYSAUDQSR-UHFFFAOYSA-N (2-tert-butylphenyl)urea Chemical compound CC(C)(C)C1=CC=CC=C1NC(N)=O ABECWVYSAUDQSR-UHFFFAOYSA-N 0.000 description 1
- PPCUBWWPGYHEJE-UHFFFAOYSA-N (3-chlorophenyl)urea Chemical compound NC(=O)NC1=CC=CC(Cl)=C1 PPCUBWWPGYHEJE-UHFFFAOYSA-N 0.000 description 1
- LEMWRPPGMBWTMD-UHFFFAOYSA-N (3-ethoxyphenyl)urea Chemical compound CCOC1=CC=CC(NC(N)=O)=C1 LEMWRPPGMBWTMD-UHFFFAOYSA-N 0.000 description 1
- IPRCBIWIPMJXIK-UHFFFAOYSA-N (3-hydroxyphenyl)urea Chemical compound NC(=O)NC1=CC=CC(O)=C1 IPRCBIWIPMJXIK-UHFFFAOYSA-N 0.000 description 1
- WDHPVLQWHRHMEY-UHFFFAOYSA-N (3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(N)=O)=C1 WDHPVLQWHRHMEY-UHFFFAOYSA-N 0.000 description 1
- UVQVMNIYFXZXCI-UHFFFAOYSA-N (3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(N)=O)=C1 UVQVMNIYFXZXCI-UHFFFAOYSA-N 0.000 description 1
- RECCURWJDVZHIH-UHFFFAOYSA-N (4-chlorophenyl)urea Chemical compound NC(=O)NC1=CC=C(Cl)C=C1 RECCURWJDVZHIH-UHFFFAOYSA-N 0.000 description 1
- DMSHKWHLXNDUST-UHFFFAOYSA-N (4-methylphenyl)urea Chemical compound CC1=CC=C(NC(N)=O)C=C1 DMSHKWHLXNDUST-UHFFFAOYSA-N 0.000 description 1
- PJOCMQUXXAJFKU-UHFFFAOYSA-N (4-propan-2-yloxyphenyl)urea Chemical compound CC(C)OC1=CC=C(NC(N)=O)C=C1 PJOCMQUXXAJFKU-UHFFFAOYSA-N 0.000 description 1
- HEUDNCPBUYZJDR-UHFFFAOYSA-N 1,1-dimethyl-3-(2-methylphenyl)urea Chemical compound CN(C)C(=O)NC1=CC=CC=C1C HEUDNCPBUYZJDR-UHFFFAOYSA-N 0.000 description 1
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 1
- WVYBLYKUAKXDLA-UHFFFAOYSA-N 1,3-bis(2-methylphenyl)urea Chemical compound CC1=CC=CC=C1NC(=O)NC1=CC=CC=C1C WVYBLYKUAKXDLA-UHFFFAOYSA-N 0.000 description 1
- DAHDILBFGCYNEF-UHFFFAOYSA-N 1,3-diethyl-1-phenylurea Chemical compound CCNC(=O)N(CC)C1=CC=CC=C1 DAHDILBFGCYNEF-UHFFFAOYSA-N 0.000 description 1
- SGXQPTCGTJXMME-UHFFFAOYSA-N 1,3-dimethyl-1-(2-methylphenyl)urea Chemical compound CNC(=O)N(C)C1=CC=CC=C1C SGXQPTCGTJXMME-UHFFFAOYSA-N 0.000 description 1
- ZWOULFZCQXICLZ-UHFFFAOYSA-N 1,3-dimethyl-1-phenylurea Chemical compound CNC(=O)N(C)C1=CC=CC=C1 ZWOULFZCQXICLZ-UHFFFAOYSA-N 0.000 description 1
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- GLAQLBSPTKQTEY-UHFFFAOYSA-N 1-(2-chloroethyl)-3-phenylurea Chemical compound ClCCNC(=O)NC1=CC=CC=C1 GLAQLBSPTKQTEY-UHFFFAOYSA-N 0.000 description 1
- ALRCNDQTWIMINP-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-ethylurea Chemical compound CCNC(=O)NC1=CC=CC=C1Cl ALRCNDQTWIMINP-UHFFFAOYSA-N 0.000 description 1
- VCVLJVCEIIJNSJ-UHFFFAOYSA-N 1-(3-chlorophenyl)-1-methylurea Chemical compound NC(=O)N(C)C1=CC=CC(Cl)=C1 VCVLJVCEIIJNSJ-UHFFFAOYSA-N 0.000 description 1
- DRUOVNJVALTABZ-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-1,3-dimethylurea Chemical compound CCOc1ccc(cc1)N(C)C(=O)NC DRUOVNJVALTABZ-UHFFFAOYSA-N 0.000 description 1
- FMZVAQGPUASACA-UHFFFAOYSA-N 1-(4-methoxyphenyl)-1-methylurea Chemical compound COC1=CC=C(N(C)C(N)=O)C=C1 FMZVAQGPUASACA-UHFFFAOYSA-N 0.000 description 1
- QTFLMROKAFFGMF-UHFFFAOYSA-N 1-(5-hydroxypentyl)-3-phenylurea Chemical compound OCCCCCNC(=O)NC1=CC=CC=C1 QTFLMROKAFFGMF-UHFFFAOYSA-N 0.000 description 1
- KZOFCHITIRGEGY-UHFFFAOYSA-N 1-cyclohexyl-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1CCCCC1 KZOFCHITIRGEGY-UHFFFAOYSA-N 0.000 description 1
- WPLYTRWMCWBZEN-UHFFFAOYSA-N 1-cyclohexyl-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1CCCCC1 WPLYTRWMCWBZEN-UHFFFAOYSA-N 0.000 description 1
- KMFGLEGMDZJEEJ-UHFFFAOYSA-N 1-cyclohexyloxy-1-phenylurea Chemical compound C=1C=CC=CC=1N(C(=O)N)OC1CCCCC1 KMFGLEGMDZJEEJ-UHFFFAOYSA-N 0.000 description 1
- ZVZVXCQEGGRZSC-UHFFFAOYSA-N 1-ethyl-1,3-dimethyl-3-phenylurea Chemical compound CCN(C)C(=O)N(C)C1=CC=CC=C1 ZVZVXCQEGGRZSC-UHFFFAOYSA-N 0.000 description 1
- SWQFOFLNFYIHFV-UHFFFAOYSA-N 1-ethyl-3,3-dimethyl-1-phenylurea Chemical compound CN(C)C(=O)N(CC)C1=CC=CC=C1 SWQFOFLNFYIHFV-UHFFFAOYSA-N 0.000 description 1
- FPDWKUHNOAAQSO-UHFFFAOYSA-N 1-ethyl-3-(2-methoxyphenyl)urea Chemical compound CCNC(=O)NC1=CC=CC=C1OC FPDWKUHNOAAQSO-UHFFFAOYSA-N 0.000 description 1
- RLGZENVXTXVWJN-UHFFFAOYSA-N 1-methyl-1,3-diphenylurea Chemical compound C=1C=CC=CC=1N(C)C(=O)NC1=CC=CC=C1 RLGZENVXTXVWJN-UHFFFAOYSA-N 0.000 description 1
- SKAADKSETAYKGL-UHFFFAOYSA-N 1-methyl-1-phenylurea Chemical compound NC(=O)N(C)C1=CC=CC=C1 SKAADKSETAYKGL-UHFFFAOYSA-N 0.000 description 1
- ACOZWFISMVUEHN-UHFFFAOYSA-N 3-(4-ethoxyphenyl)-1,1-dimethylurea Chemical compound CCOC1=CC=C(NC(=O)N(C)C)C=C1 ACOZWFISMVUEHN-UHFFFAOYSA-N 0.000 description 1
- BWXGHCNBJQHNNL-UHFFFAOYSA-N 3-cyclohexyl-1-ethyl-1-phenylurea Chemical compound C=1C=CC=CC=1N(CC)C(=O)NC1CCCCC1 BWXGHCNBJQHNNL-UHFFFAOYSA-N 0.000 description 1
- ILNGCUVXLQVDTC-UHFFFAOYSA-N 4-chloromorpholine Chemical compound ClN1CCOCC1 ILNGCUVXLQVDTC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DPRNGQDPBFKLCK-UHFFFAOYSA-N [4-(carbamoylamino)phenyl]urea Chemical compound NC(=O)NC1=CC=C(NC(N)=O)C=C1 DPRNGQDPBFKLCK-UHFFFAOYSA-N 0.000 description 1
- WYRSGHWXCTZGJM-UHFFFAOYSA-N [4-[(2-methylpropan-2-yl)oxy]phenyl]urea Chemical compound CC(C)(C)OC1=CC=C(NC(N)=O)C=C1 WYRSGHWXCTZGJM-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- PZIMIYVOZBTARW-UHFFFAOYSA-N centralite Chemical compound C=1C=CC=CC=1N(CC)C(=O)N(CC)C1=CC=CC=C1 PZIMIYVOZBTARW-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine 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
- 239000007788 liquid Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- DJEKCANOAKSYPG-UHFFFAOYSA-N n-(chloromethyl)-1-phenylmethanamine Chemical compound ClCNCC1=CC=CC=C1 DJEKCANOAKSYPG-UHFFFAOYSA-N 0.000 description 1
- POOMBLVZFRPIBC-UHFFFAOYSA-N n-(chloromethyl)ethanamine Chemical compound CCNCCl POOMBLVZFRPIBC-UHFFFAOYSA-N 0.000 description 1
- PZTLKMFVSJYYOZ-UHFFFAOYSA-N n-[4-(carbamoylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(NC(N)=O)C=C1 PZTLKMFVSJYYOZ-UHFFFAOYSA-N 0.000 description 1
- TYDFLVGVWMSQAC-UHFFFAOYSA-N n-chloro-n-ethylethanamine Chemical compound CCN(Cl)CC TYDFLVGVWMSQAC-UHFFFAOYSA-N 0.000 description 1
- QXJIABOUHLYVHP-UHFFFAOYSA-N n-chloromethanamine Chemical compound CNCl QXJIABOUHLYVHP-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1909377A IT1076004B (it) | 1977-01-07 | 1977-01-07 | Procedimento per la preparazione di ammino-fenil-uree |
| IT2026277A IT1075118B (it) | 1977-02-14 | 1977-02-14 | Procedimento per la preparazione di ammino-carbanilati |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2800111A1 true DE2800111A1 (de) | 1978-07-13 |
Family
ID=26327047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782800111 Withdrawn DE2800111A1 (de) | 1977-01-07 | 1978-01-03 | Verfahren zur herstellung von aminophenylharnstoffen und aminocarbanylaten |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS53124237A (enrdf_load_stackoverflow) |
| CA (1) | CA1092125A (enrdf_load_stackoverflow) |
| DE (1) | DE2800111A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2376841A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1554543A (enrdf_load_stackoverflow) |
| NL (1) | NL7800026A (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1067024B (it) * | 1976-11-17 | 1985-03-12 | Acna | Procedimento per la preparazione di ammine aromatiche |
| OA07768A (fr) * | 1983-05-12 | 1985-08-30 | Sumitomo Chemical Co | Dérivés d'anillines fongicides. |
| SE9802209D0 (sv) * | 1998-06-22 | 1998-06-22 | Astra Pharma Inc | Novel compounds |
| JP2004516238A (ja) * | 2000-06-21 | 2004-06-03 | ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー | ケモカイン受容体活性調節剤としてのｎ−ウレイドアルキル−ピペリジン |
| AU2005260495B2 (en) * | 2004-07-02 | 2009-04-30 | Sankyo Company, Limited | Urea derivative |
| BRPI0913986A2 (pt) | 2008-03-26 | 2015-10-20 | Daiichi Sankyo Co Ltd | composto, composição farmacêutica, e, uso de um composto |
-
1978
- 1978-01-02 NL NL7800026A patent/NL7800026A/xx not_active Application Discontinuation
- 1978-01-03 DE DE19782800111 patent/DE2800111A1/de not_active Withdrawn
- 1978-01-04 GB GB16178A patent/GB1554543A/en not_active Expired
- 1978-01-04 FR FR7800113A patent/FR2376841A1/fr active Granted
- 1978-01-06 JP JP29078A patent/JPS53124237A/ja active Pending
- 1978-01-06 CA CA294,489A patent/CA1092125A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2376841B1 (enrdf_load_stackoverflow) | 1981-10-09 |
| FR2376841A1 (fr) | 1978-08-04 |
| CA1092125A (en) | 1980-12-23 |
| NL7800026A (nl) | 1978-07-11 |
| GB1554543A (en) | 1979-10-24 |
| JPS53124237A (en) | 1978-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2855764C2 (enrdf_load_stackoverflow) | ||
| DE2503187A1 (de) | Verfahren zur herstellung durch chlor meta-substituierte aniline | |
| DE2129200A1 (de) | Verfahren zur Herstellung von N-Arylharnstoffen | |
| DE2800111A1 (de) | Verfahren zur herstellung von aminophenylharnstoffen und aminocarbanylaten | |
| DE3634717A1 (de) | Verfahren zur herstellung von 5-methyltetrazol | |
| DE60110807T2 (de) | Kontinuierliches verfahren zur herstellung von pestiziden chlorthiazolen | |
| EP0368008A1 (de) | Fluor enthaltende Phenole | |
| DE2363458B2 (de) | Aminobenzaldehydverbindungen und ein Verfahren zu ihrer Herstellung | |
| DE3332687A1 (de) | Verfahren zur herstellung von 2-amino-alkylpyridinen | |
| DE2814860A1 (de) | Verfahren zur herstellung von aromatischen aminen | |
| EP0005276A2 (de) | Verfahren zur Herstellung von Monoarylthioharnstoffen | |
| DE3607298A1 (de) | Verfahren zur herstellung von benzoylharnstoffen | |
| DE2719020A1 (de) | Verfahren zur herstellung von anthranilamiden | |
| EP0551632A2 (de) | Verfahren zur Herstellung von Halogenanthranilsäuren | |
| DE69526173T2 (de) | Verfahren zur Herstellung von Oxyindolen | |
| DD236520A5 (de) | Verfahren zur herstellung von chlor-o-nitroanilinen | |
| EP0022959B1 (de) | Verfahren zur Herstellung von Diazoniumtetrafluoroboraten in verdünnter wässriger Lösung | |
| DE3340348A1 (de) | Verfahren zur herstellung von (4-amino-2-chlor-5-alkylphenyl)-(alpha)-(4-chlorphenyl)-acetonitril | |
| DE2440238A1 (de) | Verfahren zur herstellung von organischen hydrazinen | |
| DE2529549C3 (de) | Verfahren zur Herstellung von Phenylisopropylharnstoffen | |
| DE664995C (de) | Verfahren zur Darstellung von Thiazthioniumchloriden | |
| DE1493965C (de) | Verfahren zum Herstellen von Racema ten optisch aktiver Nitrile | |
| DE4102337A1 (de) | Verfahren zur herstellung von zink-bis-(dibenzyldithiocarbamat) | |
| EP0688763A1 (de) | Verfahren zur Herstellung von Hydroxycarbonsäureaniliden | |
| DE2304587A1 (de) | Beta-amino-beta-imino-propionsaeureester |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |