DE1668557B2 - Verfahren zur herstellung des 2- benzimidazol-carbaminsaeuremethylesters - Google Patents
Verfahren zur herstellung des 2- benzimidazol-carbaminsaeuremethylestersInfo
- Publication number
- DE1668557B2 DE1668557B2 DE1967P0043394 DEP0043394A DE1668557B2 DE 1668557 B2 DE1668557 B2 DE 1668557B2 DE 1967P0043394 DE1967P0043394 DE 1967P0043394 DE P0043394 A DEP0043394 A DE P0043394A DE 1668557 B2 DE1668557 B2 DE 1668557B2
- Authority
- DE
- Germany
- Prior art keywords
- cyanamide
- parts
- methyl
- reaction
- stage
- 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.)
- Granted
Links
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000012429 reaction media Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 21
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 13
- -1 alkaline earth metal cyanamide salt Chemical class 0.000 description 13
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 150000001340 alkali metals Chemical class 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- ZSYJMXLJNPEAGP-UHFFFAOYSA-N methyl n-cyanocarbamate Chemical compound COC(=O)NC#N ZSYJMXLJNPEAGP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 5
- 150000001912 cyanamides Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 150000001339 alkali metal compounds Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical compound C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 description 2
- MVXMNHYVCLMLDD-UHFFFAOYSA-N 4-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=C(C=O)C2=C1 MVXMNHYVCLMLDD-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
- 159000000007 calcium salts Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 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
- 238000010992 reflux Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 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
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling 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
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 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
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 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
- MCLITRXWHZUNCQ-UHFFFAOYSA-N methylcyanamide Chemical class CNC#N MCLITRXWHZUNCQ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 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
- 230000020477 pH reduction Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 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
- 239000000376 reactant Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005406 washing Methods 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 (2)
| Publication Number | Publication Date |
|---|---|
| DE1668557A1 DE1668557A1 (de) | 1971-01-21 |
| DE1668557B2 true DE1668557B2 (de) | 1977-04-28 |
Family
ID=27081960
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967P0043394 Granted DE1668557B2 (de) | 1966-11-15 | 1967-11-14 | Verfahren zur herstellung des 2- benzimidazol-carbaminsaeuremethylesters |
| 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 |
Family Applications After (2)
| 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 |
Country Status (16)
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 AT735570A patent/AT296330B/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
- 1967-11-10 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 NO NO17051867A patent/NO123460B/no unknown
- 1967-11-14 DE DE1967P0043394 patent/DE1668557B2/de active Granted
- 1967-11-14 DE DE19671795849 patent/DE1795849C3/de not_active Expired
- 1967-11-14 GB GB5177967A patent/GB1185237A/en not_active Expired
- 1967-11-14 NL NL6715433A patent/NL6715433A/xx unknown
- 1967-11-14 DE DE19671793733 patent/DE1793733A1/de active Pending
- 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 DK DK568667A patent/DK132078C/da active
- 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 |
|---|---|
| IL28858A (en) | 1971-08-25 |
| BE706519A (enrdf_load_stackoverflow) | 1968-03-18 |
| LU54805A1 (enrdf_load_stackoverflow) | 1968-01-31 |
| FI48736C (fi) | 1974-12-10 |
| ES347053A1 (es) | 1969-05-16 |
| DE1793733A1 (de) | 1973-03-01 |
| YU33788B (en) | 1978-05-15 |
| AT286311B (de) | 1970-12-10 |
| DK120286B (da) | 1971-05-10 |
| NO123460B (enrdf_load_stackoverflow) | 1971-11-22 |
| NL6715433A (enrdf_load_stackoverflow) | 1968-05-16 |
| DK132078C (da) | 1976-03-15 |
| DE1795849C3 (de) | 1979-03-01 |
| FI48736B (enrdf_load_stackoverflow) | 1974-09-02 |
| DE1795849B2 (de) | 1978-06-29 |
| CH547291A (de) | 1974-03-29 |
| DE1795849A1 (de) | 1977-02-24 |
| AT296330B (de) | 1972-02-10 |
| DE1668557A1 (de) | 1971-01-21 |
| DK132078B (da) | 1975-10-20 |
| BR6794666D0 (pt) | 1973-05-15 |
| YU222767A (en) | 1977-10-31 |
| GB1185237A (en) | 1970-03-25 |
| SE342227B (enrdf_load_stackoverflow) | 1972-01-31 |
| DOP1967001423A (es) | 1972-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |