IL34611A - Process for the preparation of benzimidazole-2-carbamic acid esters - Google Patents
Process for the preparation of benzimidazole-2-carbamic acid estersInfo
- Publication number
- IL34611A IL34611A IL7034611A IL3461170A IL34611A IL 34611 A IL34611 A IL 34611A IL 7034611 A IL7034611 A IL 7034611A IL 3461170 A IL3461170 A IL 3461170A IL 34611 A IL34611 A IL 34611A
- Authority
- IL
- Israel
- Prior art keywords
- acid esters
- preparation
- benzimidazole
- carbamic acid
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 3
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 6
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical compound Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- -1 methyl isopropyl ester Chemical class 0.000 description 2
- OUQFCBDRFYTHKG-UHFFFAOYSA-N n-(dichloromethylidene)carbamoyl chloride Chemical compound ClC(Cl)=NC(Cl)=O OUQFCBDRFYTHKG-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- WWPPGEJAMWSVJJ-UHFFFAOYSA-N [Na].[K].[K] Chemical compound [Na].[K].[K] WWPPGEJAMWSVJJ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- BVAAXYHEQRTUMO-UHFFFAOYSA-N ethyl n-(dichloromethylidene)carbamate Chemical compound CCOC(=O)N=C(Cl)Cl BVAAXYHEQRTUMO-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FURSOPUPGJBTMU-UHFFFAOYSA-N methyl isocyanoformate Chemical compound COC(=O)[N+]#[C-] FURSOPUPGJBTMU-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1932297A DE1932297C3 (de) | 1969-06-26 | 1969-06-26 | Verfahren zur Herstellung von Benzimidazol -2-carbaminsäureestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL34611A0 IL34611A0 (en) | 1970-07-19 |
| IL34611A true IL34611A (en) | 1973-01-30 |
Family
ID=5738008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL7034611A IL34611A (en) | 1969-06-26 | 1970-05-27 | Process for the preparation of benzimidazole-2-carbamic acid esters |
Country Status (12)
| Country | Link |
|---|---|
| BE (1) | BE752513A (enExample) |
| BG (1) | BG17319A3 (enExample) |
| CA (1) | CA937935A (enExample) |
| CH (1) | CH529139A (enExample) |
| DE (1) | DE1932297C3 (enExample) |
| ES (1) | ES381154A1 (enExample) |
| FR (1) | FR2051372A5 (enExample) |
| GB (1) | GB1256834A (enExample) |
| IL (1) | IL34611A (enExample) |
| NL (1) | NL7008954A (enExample) |
| SE (1) | SE352633B (enExample) |
| ZA (1) | ZA703598B (enExample) |
Families Citing this family (4)
| 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 |
| HU169503B (enExample) * | 1974-02-05 | 1976-12-28 | ||
| DE2441201C2 (de) * | 1974-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung |
| DE3705084A1 (de) * | 1987-02-18 | 1988-09-01 | Hoechst Ag | Verfahren zur herstellung von pyrimidinen |
-
1969
- 1969-06-26 DE DE1932297A patent/DE1932297C3/de not_active Expired
-
1970
- 1970-05-27 ZA ZA703598A patent/ZA703598B/xx unknown
- 1970-05-27 IL IL7034611A patent/IL34611A/en unknown
- 1970-05-27 CH CH787070A patent/CH529139A/de not_active IP Right Cessation
- 1970-06-02 CA CA084373A patent/CA937935A/en not_active Expired
- 1970-06-12 BG BG014924A patent/BG17319A3/xx unknown
- 1970-06-18 NL NL7008954A patent/NL7008954A/xx not_active Application Discontinuation
- 1970-06-19 GB GB1256834D patent/GB1256834A/en not_active Expired
- 1970-06-25 SE SE08822/70A patent/SE352633B/xx unknown
- 1970-06-25 ES ES381154A patent/ES381154A1/es not_active Expired
- 1970-06-25 BE BE752513D patent/BE752513A/xx unknown
- 1970-06-26 FR FR7023754A patent/FR2051372A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1256834A (enExample) | 1971-12-15 |
| DE1932297C3 (de) | 1974-09-12 |
| FR2051372A5 (enExample) | 1971-04-02 |
| DE1932297A1 (de) | 1971-01-07 |
| DE1932297B2 (de) | 1974-01-24 |
| SE352633B (enExample) | 1973-01-08 |
| ZA703598B (en) | 1971-01-27 |
| IL34611A0 (en) | 1970-07-19 |
| BG17319A3 (bg) | 1973-07-25 |
| NL7008954A (enExample) | 1970-12-29 |
| CH529139A (de) | 1972-10-15 |
| CA937935A (en) | 1973-12-04 |
| BE752513A (fr) | 1970-12-28 |
| ES381154A1 (es) | 1972-11-16 |
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