DE1956157A1 - Verfahren zur Herstellung von substituierten 1-Carbamoyl-2-benzimidazolcarbamaten - Google Patents
Verfahren zur Herstellung von substituierten 1-Carbamoyl-2-benzimidazolcarbamatenInfo
- Publication number
- DE1956157A1 DE1956157A1 DE19691956157 DE1956157A DE1956157A1 DE 1956157 A1 DE1956157 A1 DE 1956157A1 DE 19691956157 DE19691956157 DE 19691956157 DE 1956157 A DE1956157 A DE 1956157A DE 1956157 A1 DE1956157 A1 DE 1956157A1
- Authority
- DE
- Germany
- Prior art keywords
- ethyl ketone
- methyl
- parts
- benzimidazole
- methyl ethyl
- 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 22
- 238000002360 preparation method Methods 0.000 title claims description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 93
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 21
- -1 2-benzimidazole carbamates Chemical class 0.000 claims description 17
- 239000012948 isocyanate Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000002513 isocyanates Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- UYWWLYCGNNCLKE-UHFFFAOYSA-N 2-pyridin-4-yl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C1=CC=NC=C1 UYWWLYCGNNCLKE-UHFFFAOYSA-N 0.000 claims description 11
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 5
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 24
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 10
- 239000000417 fungicide Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 239000012066 reaction slurry Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- URANHGZOFVYVJV-UHFFFAOYSA-N 1h-benzimidazole;methyl carbamate Chemical compound COC(N)=O.C1=CC=C2NC=NC2=C1 URANHGZOFVYVJV-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- LPRSRULGRPUBTD-UHFFFAOYSA-N butan-2-one;hydrate Chemical compound O.CCC(C)=O LPRSRULGRPUBTD-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77452868A | 1968-11-08 | 1968-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1956157A1 true DE1956157A1 (de) | 1970-06-04 |
Family
ID=25101519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691956157 Pending DE1956157A1 (de) | 1968-11-08 | 1969-11-07 | Verfahren zur Herstellung von substituierten 1-Carbamoyl-2-benzimidazolcarbamaten |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4838709B1 (enrdf_load_stackoverflow) |
| BE (1) | BE741429A (enrdf_load_stackoverflow) |
| DE (1) | DE1956157A1 (enrdf_load_stackoverflow) |
| ES (1) | ES373164A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2022902A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1238977A (enrdf_load_stackoverflow) |
| IL (1) | IL33182A (enrdf_load_stackoverflow) |
| NL (1) | NL6916002A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2618853A1 (de) * | 1975-05-06 | 1976-11-18 | Chinoin Gyogyszer Es Vegyeszet | Verfahren zur herstellung von karbamat- und harnstoff-derivaten |
| DE2726734A1 (de) * | 1977-06-14 | 1979-01-11 | Estra Normteile & Masch | Planeinstechwerkzeug |
-
1969
- 1969-10-14 IL IL33182A patent/IL33182A/xx unknown
- 1969-10-23 NL NL6916002A patent/NL6916002A/xx unknown
- 1969-10-28 GB GB1238977D patent/GB1238977A/en not_active Expired
- 1969-11-04 ES ES373164A patent/ES373164A1/es not_active Expired
- 1969-11-05 JP JP44088153A patent/JPS4838709B1/ja active Pending
- 1969-11-07 BE BE741429D patent/BE741429A/xx unknown
- 1969-11-07 FR FR6938434A patent/FR2022902A1/fr active Pending
- 1969-11-07 DE DE19691956157 patent/DE1956157A1/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2618853A1 (de) * | 1975-05-06 | 1976-11-18 | Chinoin Gyogyszer Es Vegyeszet | Verfahren zur herstellung von karbamat- und harnstoff-derivaten |
| DE2726734A1 (de) * | 1977-06-14 | 1979-01-11 | Estra Normteile & Masch | Planeinstechwerkzeug |
Also Published As
| Publication number | Publication date |
|---|---|
| IL33182A (en) | 1972-05-30 |
| GB1238977A (enrdf_load_stackoverflow) | 1971-07-14 |
| IL33182A0 (en) | 1969-12-31 |
| BE741429A (enrdf_load_stackoverflow) | 1970-04-16 |
| ES373164A1 (es) | 1971-12-16 |
| JPS4838709B1 (enrdf_load_stackoverflow) | 1973-11-19 |
| NL6916002A (enrdf_load_stackoverflow) | 1970-05-12 |
| FR2022902A1 (enrdf_load_stackoverflow) | 1970-08-07 |
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