DE1795849C3 - Verfahren zur Herstellung des 2-Benzimidazol-carbaminsäuremethylesters - Google Patents
Verfahren zur Herstellung des 2-Benzimidazol-carbaminsäuremethylestersInfo
- Publication number
- DE1795849C3 DE1795849C3 DE19671795849 DE1795849A DE1795849C3 DE 1795849 C3 DE1795849 C3 DE 1795849C3 DE 19671795849 DE19671795849 DE 19671795849 DE 1795849 A DE1795849 A DE 1795849A DE 1795849 C3 DE1795849 C3 DE 1795849C3
- Authority
- DE
- Germany
- Prior art keywords
- benzimidazole
- carbamic acid
- preparation
- parts
- methyl ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 6
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- -1 alkyl chloroformate Chemical compound 0.000 description 4
- ZSYJMXLJNPEAGP-UHFFFAOYSA-N methyl n-cyanocarbamate Chemical compound COC(=O)NC#N ZSYJMXLJNPEAGP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241000357437 Mola Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical class CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 150000004987 o-phenylenediamines Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59438466A | 1966-11-15 | 1966-11-15 | |
| US67473967A | 1967-10-12 | 1967-10-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1795849A1 DE1795849A1 (de) | 1977-02-24 |
| DE1795849B2 DE1795849B2 (de) | 1978-06-29 |
| DE1795849C3 true DE1795849C3 (de) | 1979-03-01 |
Family
ID=27081960
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671795849 Expired DE1795849C3 (de) | 1966-11-15 | 1967-11-14 | Verfahren zur Herstellung des 2-Benzimidazol-carbaminsäuremethylesters |
| DE19671793733 Pending DE1793733A1 (de) | 1966-11-15 | 1967-11-14 | Salze von alkylcyancarbamaten mit o-phenylendiaminen, verfahren zu ihrer herstellung und solche verbindungen enthaltende mittel |
| DE1967P0043394 Granted DE1668557B2 (de) | 1966-11-15 | 1967-11-14 | Verfahren zur herstellung des 2- benzimidazol-carbaminsaeuremethylesters |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671793733 Pending DE1793733A1 (de) | 1966-11-15 | 1967-11-14 | Salze von alkylcyancarbamaten mit o-phenylendiaminen, verfahren zu ihrer herstellung und solche verbindungen enthaltende mittel |
| DE1967P0043394 Granted DE1668557B2 (de) | 1966-11-15 | 1967-11-14 | Verfahren zur herstellung des 2- benzimidazol-carbaminsaeuremethylesters |
Country Status (16)
| Country | Link |
|---|---|
| AT (2) | AT286311B (enExample) |
| BE (1) | BE706519A (enExample) |
| BR (1) | BR6794666D0 (enExample) |
| CH (1) | CH547291A (enExample) |
| DE (3) | DE1795849C3 (enExample) |
| DK (2) | DK132078C (enExample) |
| DO (1) | DOP1967001423A (enExample) |
| ES (1) | ES347053A1 (enExample) |
| FI (1) | FI48736C (enExample) |
| GB (1) | GB1185237A (enExample) |
| IL (1) | IL28858A (enExample) |
| LU (1) | LU54805A1 (enExample) |
| NL (1) | NL6715433A (enExample) |
| NO (1) | NO123460B (enExample) |
| SE (1) | SE342227B (enExample) |
| YU (1) | YU33788B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2227919C2 (de) * | 1972-06-08 | 1982-12-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Benzimidazol-2-yl-carbaminsäure-methylester |
| DE3323024A1 (de) * | 1983-06-25 | 1985-01-03 | Hoechst Ag, 6230 Frankfurt | Verfahren zur verminderung von nebenproduktanteilen bei der herstellung von carbendazim |
-
1967
- 1967-10-30 IL IL2885867A patent/IL28858A/en unknown
- 1967-11-07 LU LU54805D patent/LU54805A1/xx unknown
- 1967-11-08 CH CH547291D patent/CH547291A/de not_active IP Right Cessation
- 1967-11-09 AT AT1007667A patent/AT286311B/de not_active IP Right Cessation
- 1967-11-09 DO DO1967001423A patent/DOP1967001423A/es unknown
- 1967-11-09 AT AT735570A patent/AT296330B/de not_active IP Right Cessation
- 1967-11-10 SE SE1543667A patent/SE342227B/xx unknown
- 1967-11-11 ES ES347053A patent/ES347053A1/es not_active Expired
- 1967-11-13 BR BR19466667A patent/BR6794666D0/pt unknown
- 1967-11-14 NL NL6715433A patent/NL6715433A/xx unknown
- 1967-11-14 DK DK568667A patent/DK132078C/da active
- 1967-11-14 GB GB5177967A patent/GB1185237A/en not_active Expired
- 1967-11-14 NO NO17051867A patent/NO123460B/no unknown
- 1967-11-14 DE DE19671795849 patent/DE1795849C3/de not_active Expired
- 1967-11-14 BE BE706519D patent/BE706519A/xx not_active IP Right Cessation
- 1967-11-14 FI FI306567A patent/FI48736C/fi active
- 1967-11-14 DE DE19671793733 patent/DE1793733A1/de active Pending
- 1967-11-14 DE DE1967P0043394 patent/DE1668557B2/de active Granted
- 1967-11-15 YU YU222767A patent/YU33788B/xx unknown
-
1968
- 1968-10-29 DK DK523968A patent/DK120286B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6715433A (enExample) | 1968-05-16 |
| FI48736B (enExample) | 1974-09-02 |
| YU222767A (en) | 1977-10-31 |
| DE1795849B2 (de) | 1978-06-29 |
| NO123460B (enExample) | 1971-11-22 |
| DE1793733A1 (de) | 1973-03-01 |
| BE706519A (enExample) | 1968-03-18 |
| DK132078B (da) | 1975-10-20 |
| IL28858A (en) | 1971-08-25 |
| SE342227B (enExample) | 1972-01-31 |
| BR6794666D0 (pt) | 1973-05-15 |
| DE1668557B2 (de) | 1977-04-28 |
| AT286311B (de) | 1970-12-10 |
| DOP1967001423A (es) | 1972-12-13 |
| FI48736C (fi) | 1974-12-10 |
| DE1668557A1 (de) | 1971-01-21 |
| DK132078C (da) | 1976-03-15 |
| LU54805A1 (enExample) | 1968-01-31 |
| ES347053A1 (es) | 1969-05-16 |
| DE1795849A1 (de) | 1977-02-24 |
| CH547291A (de) | 1974-03-29 |
| GB1185237A (en) | 1970-03-25 |
| DK120286B (da) | 1971-05-10 |
| AT296330B (de) | 1972-02-10 |
| YU33788B (en) | 1978-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |