NO123460B - - Google Patents
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- Publication number
- NO123460B NO123460B NO17051867A NO17051867A NO123460B NO 123460 B NO123460 B NO 123460B NO 17051867 A NO17051867 A NO 17051867A NO 17051867 A NO17051867 A NO 17051867A NO 123460 B NO123460 B NO 123460B
- Authority
- NO
- Norway
- Prior art keywords
- reaction
- cyanamide
- alkyl
- phenylenediamine
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 24
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 21
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 20
- -1 alkyl chloroformate Chemical compound 0.000 claims description 17
- 150000001912 cyanamides Chemical class 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 5
- ZSYJMXLJNPEAGP-UHFFFAOYSA-N methyl n-cyanocarbamate Chemical compound COC(=O)NC#N ZSYJMXLJNPEAGP-UHFFFAOYSA-N 0.000 description 5
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000000725 suspension 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
- 230000035484 reaction time Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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
- OKOVSTKGUBOSTB-UHFFFAOYSA-N N-(1H-benzimidazol-2-yl)carbamic acid ethyl ester Chemical compound C1=CC=C2NC(NC(=O)OCC)=NC2=C1 OKOVSTKGUBOSTB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 150000007513 acids Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012265 solid product Substances 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- YCQZDRXPYGNHMP-UHFFFAOYSA-N [Na].COC(=O)NC#N Chemical compound [Na].COC(=O)NC#N YCQZDRXPYGNHMP-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- VMHMVHBOHRQSMG-UHFFFAOYSA-N chloromethane formic acid Chemical compound C(=O)O.CCl VMHMVHBOHRQSMG-UHFFFAOYSA-N 0.000 description 1
- 235000019987 cider Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- NJKCXLDGDRHSMV-UHFFFAOYSA-N cyanamide;hydrate Chemical compound O.NC#N NJKCXLDGDRHSMV-UHFFFAOYSA-N 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
- 230000000694 effects Effects 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- ISLRUKSSARPVLK-UHFFFAOYSA-N ethyl n-cyanocarbamate;sodium Chemical compound [Na].CCOC(=O)NC#N ISLRUKSSARPVLK-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical class CSC(N)=N SDDKIZNHOCEXTF-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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006276 transfer reaction 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 (1)
| Publication Number | Publication Date |
|---|---|
| NO123460B true NO123460B (d) | 1971-11-22 |
Family
ID=27081960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO17051867A NO123460B (d) | 1966-11-15 | 1967-11-14 |
Country Status (16)
| Country | Link |
|---|---|
| AT (2) | AT296330B (d) |
| BE (1) | BE706519A (d) |
| BR (1) | BR6794666D0 (d) |
| CH (1) | CH547291A (d) |
| DE (3) | DE1668557B2 (d) |
| DK (2) | DK132078C (d) |
| DO (1) | DOP1967001423A (d) |
| ES (1) | ES347053A1 (d) |
| FI (1) | FI48736C (d) |
| GB (1) | GB1185237A (d) |
| IL (1) | IL28858A (d) |
| LU (1) | LU54805A1 (d) |
| NL (1) | NL6715433A (d) |
| NO (1) | NO123460B (d) |
| SE (1) | SE342227B (d) |
| YU (1) | YU33788B (d) |
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 DO DO1967001423A patent/DOP1967001423A/es unknown
- 1967-11-09 AT AT1007667A patent/AT286311B/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 NO NO17051867A patent/NO123460B/no unknown
- 1967-11-14 DE DE1967P0043394 patent/DE1668557B2/de active Granted
- 1967-11-14 GB GB5177967A patent/GB1185237A/en not_active Expired
- 1967-11-14 FI FI306567A patent/FI48736C/fi active
- 1967-11-14 DE DE19671795849 patent/DE1795849C3/de not_active Expired
- 1967-11-14 DK DK568667A patent/DK132078C/da active
- 1967-11-14 DE DE19671793733 patent/DE1793733A1/de active Pending
- 1967-11-14 NL NL6715433A patent/NL6715433A/xx unknown
- 1967-11-14 BE BE706519D patent/BE706519A/xx not_active IP Right Cessation
- 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 |
|---|---|
| GB1185237A (en) | 1970-03-25 |
| LU54805A1 (d) | 1968-01-31 |
| DE1795849C3 (de) | 1979-03-01 |
| CH547291A (de) | 1974-03-29 |
| DK132078C (da) | 1976-03-15 |
| YU33788B (en) | 1978-05-15 |
| DK132078B (da) | 1975-10-20 |
| DE1668557A1 (de) | 1971-01-21 |
| ES347053A1 (es) | 1969-05-16 |
| AT296330B (de) | 1972-02-10 |
| DE1793733A1 (de) | 1973-03-01 |
| NL6715433A (d) | 1968-05-16 |
| DK120286B (da) | 1971-05-10 |
| DE1668557B2 (de) | 1977-04-28 |
| FI48736C (fi) | 1974-12-10 |
| BE706519A (d) | 1968-03-18 |
| IL28858A (en) | 1971-08-25 |
| BR6794666D0 (pt) | 1973-05-15 |
| SE342227B (d) | 1972-01-31 |
| DE1795849A1 (de) | 1977-02-24 |
| DE1795849B2 (de) | 1978-06-29 |
| FI48736B (d) | 1974-09-02 |
| DOP1967001423A (es) | 1972-12-13 |
| YU222767A (en) | 1977-10-31 |
| AT286311B (de) | 1970-12-10 |
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