DE1189980B - Verfahren zur Herstellung von Harnstoffderivaten - Google Patents
Verfahren zur Herstellung von HarnstoffderivatenInfo
- Publication number
- DE1189980B DE1189980B DEF31874A DEF0031874A DE1189980B DE 1189980 B DE1189980 B DE 1189980B DE F31874 A DEF31874 A DE F31874A DE F0031874 A DEF0031874 A DE F0031874A DE 1189980 B DE1189980 B DE 1189980B
- Authority
- DE
- Germany
- Prior art keywords
- urea
- methoxy
- methyl
- general formula
- aniline
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 19
- 150000003672 ureas Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000460 chlorine Substances 0.000 claims description 37
- -1 alkoxy urea Chemical compound 0.000 claims description 34
- 239000012429 reaction media Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 12
- 229940100198 alkylating agent Drugs 0.000 claims description 9
- 239000002168 alkylating agent Substances 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 238000002955 isolation Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000005262 alkoxyamine group Chemical group 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- 238000005804 alkylation reaction Methods 0.000 description 13
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000029936 alkylation Effects 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 6
- 235000013877 carbamide Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000001256 steam distillation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 2
- IWNHTCBFRSCBQK-UHFFFAOYSA-N 2-(2-chlorophenyl)ethanol Chemical compound OCCC1=CC=CC=C1Cl IWNHTCBFRSCBQK-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 2
- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
- KLCQXXAKURQDOV-UHFFFAOYSA-N chlorobenzene methanol Chemical compound CO.CO.ClC1=CC=CC=C1 KLCQXXAKURQDOV-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-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
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- RTQBQRBTYCSFAR-UHFFFAOYSA-N 1-methoxy-3-phenylurea Chemical compound CONC(=O)NC1=CC=CC=C1 RTQBQRBTYCSFAR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- AFSPTODSRDEZEO-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-dodecyl-1-methoxyurea Chemical compound CCCCCCCCCCCCN(OC)C(=O)NC1=CC=C(Cl)C=C1 AFSPTODSRDEZEO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GSWLTAKUCYTFGB-UHFFFAOYSA-N CCCCN(C(NC(C=C1)=CC=C1Cl)=O)OC Chemical compound CCCCN(C(NC(C=C1)=CC=C1Cl)=O)OC GSWLTAKUCYTFGB-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- DTNKCMQGOAMNGN-UHFFFAOYSA-N butan-1-ol;chlorobenzene Chemical compound CCCCO.ClC1=CC=CC=C1 DTNKCMQGOAMNGN-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WCVVIGQKJZLJDB-UHFFFAOYSA-N o-butylhydroxylamine Chemical compound CCCCON WCVVIGQKJZLJDB-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR792313A FR1220593A (fr) | 1960-08-13 | 1959-04-16 | Procédé de préparation de n-chloraryl-n'-alcoxy-n'-alcoyl-urées |
| DEF31874A DE1189980B (de) | 1960-08-13 | 1960-08-13 | Verfahren zur Herstellung von Harnstoffderivaten |
| NL267999D NL267999A (enrdf_load_stackoverflow) | 1960-08-13 | 1961-08-08 | |
| FR870796A FR83353E (fr) | 1960-08-13 | 1961-08-11 | Procédé de préparation de nu-chloraryl-nu'-alcoxy-nu'-alcoyl-urées |
| BE607204D BE607204A (enrdf_load_stackoverflow) | 1960-08-13 | 1961-08-14 | |
| GB2934061A GB994481A (en) | 1960-08-13 | 1961-08-14 | Substituted n-phenyl-n-alkoxy-n-alkyl-ureas and a process for their manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31874A DE1189980B (de) | 1960-08-13 | 1960-08-13 | Verfahren zur Herstellung von Harnstoffderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1189980B true DE1189980B (de) | 1965-04-01 |
Family
ID=7094397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF31874A Pending DE1189980B (de) | 1960-08-13 | 1960-08-13 | Verfahren zur Herstellung von Harnstoffderivaten |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE607204A (enrdf_load_stackoverflow) |
| DE (1) | DE1189980B (enrdf_load_stackoverflow) |
| FR (2) | FR1220593A (enrdf_load_stackoverflow) |
| GB (1) | GB994481A (enrdf_load_stackoverflow) |
| NL (1) | NL267999A (enrdf_load_stackoverflow) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1028986B (de) * | 1956-01-17 | 1958-04-30 | Hoechst Ag | Verfahren zur Herstellung von neuen Harnstoffderivaten |
| DE1062059B (de) * | 1957-12-05 | 1959-07-23 | Basf Ag | Mittel zur Bekaempfung unerwuenschten Pflanzenwuchses |
| DE1076117B (de) * | 1958-04-17 | 1960-02-25 | Hoechst Ag | Verfahren zur Herstellung von N-Chlorphenyl-N'-alkoxy-N'-alkylharnstoffen |
-
1959
- 1959-04-16 FR FR792313A patent/FR1220593A/fr not_active Expired
-
1960
- 1960-08-13 DE DEF31874A patent/DE1189980B/de active Pending
-
1961
- 1961-08-08 NL NL267999D patent/NL267999A/xx unknown
- 1961-08-11 FR FR870796A patent/FR83353E/fr not_active Expired
- 1961-08-14 BE BE607204D patent/BE607204A/xx unknown
- 1961-08-14 GB GB2934061A patent/GB994481A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1028986B (de) * | 1956-01-17 | 1958-04-30 | Hoechst Ag | Verfahren zur Herstellung von neuen Harnstoffderivaten |
| DE1062059B (de) * | 1957-12-05 | 1959-07-23 | Basf Ag | Mittel zur Bekaempfung unerwuenschten Pflanzenwuchses |
| DE1076117B (de) * | 1958-04-17 | 1960-02-25 | Hoechst Ag | Verfahren zur Herstellung von N-Chlorphenyl-N'-alkoxy-N'-alkylharnstoffen |
Also Published As
| Publication number | Publication date |
|---|---|
| FR83353E (fr) | 1964-07-31 |
| FR1220593A (fr) | 1960-05-25 |
| GB994481A (en) | 1965-06-10 |
| NL267999A (enrdf_load_stackoverflow) | 1964-01-27 |
| BE607204A (enrdf_load_stackoverflow) | 1962-02-14 |
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