DE2115624A1 - Verfahren zur Herstellung von o Amino benzonitrilen - Google Patents
Verfahren zur Herstellung von o Amino benzonitrilenInfo
- Publication number
- DE2115624A1 DE2115624A1 DE19712115624 DE2115624A DE2115624A1 DE 2115624 A1 DE2115624 A1 DE 2115624A1 DE 19712115624 DE19712115624 DE 19712115624 DE 2115624 A DE2115624 A DE 2115624A DE 2115624 A1 DE2115624 A1 DE 2115624A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- nitro
- phenyl
- amino
- preparation
- 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 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 Amino benzonitriles Chemical class 0.000 title 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- QYRDWARBHMCOAG-UHFFFAOYSA-N 2-amino-5-chlorobenzonitrile Chemical compound NC1=CC=C(Cl)C=C1C#N QYRDWARBHMCOAG-UHFFFAOYSA-N 0.000 description 2
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZHKNDJRPOVUPMT-UHFFFAOYSA-N 2-amino-3,5-dichlorobenzonitrile Chemical compound NC1=C(Cl)C=C(Cl)C=C1C#N ZHKNDJRPOVUPMT-UHFFFAOYSA-N 0.000 description 1
- RIYSFSQPHCAGLS-UHFFFAOYSA-N 2-amino-3,5-dinitrobenzonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C=C1[N+]([O-])=O RIYSFSQPHCAGLS-UHFFFAOYSA-N 0.000 description 1
- OATYCBHROMXWJO-UHFFFAOYSA-N 2-amino-5-bromobenzonitrile Chemical compound NC1=CC=C(Br)C=C1C#N OATYCBHROMXWJO-UHFFFAOYSA-N 0.000 description 1
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- LNWZWTFWTFMNQD-UHFFFAOYSA-N n,n'-dimethylbenzenecarboximidamide Chemical compound CNC(=NC)C1=CC=CC=C1 LNWZWTFWTFMNQD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712115624 DE2115624A1 (de) | 1971-03-31 | 1971-03-31 | Verfahren zur Herstellung von o Amino benzonitrilen |
| CH307172A CH564524A5 (enrdf_load_stackoverflow) | 1971-03-31 | 1972-03-02 | |
| NL7203765A NL7203765A (enrdf_load_stackoverflow) | 1971-03-31 | 1972-03-21 | |
| BE781275A BE781275A (fr) | 1971-03-31 | 1972-03-27 | Procede de preparation d'o-aminobenzonitriles |
| DD16189672A DD95238A5 (enrdf_load_stackoverflow) | 1971-03-31 | 1972-03-29 | |
| GB1470272A GB1377274A (en) | 1971-03-31 | 1972-03-29 | Production of o -aminobenzonitrile |
| FR7211287A FR2131750A5 (enrdf_load_stackoverflow) | 1971-03-31 | 1972-03-30 | |
| IT4935772A IT954404B (it) | 1971-03-31 | 1972-03-30 | Procedimento per la produzione di o amminobenzonitrili |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712115624 DE2115624A1 (de) | 1971-03-31 | 1971-03-31 | Verfahren zur Herstellung von o Amino benzonitrilen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2115624A1 true DE2115624A1 (de) | 1972-10-12 |
Family
ID=5803408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712115624 Pending DE2115624A1 (de) | 1971-03-31 | 1971-03-31 | Verfahren zur Herstellung von o Amino benzonitrilen |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE781275A (enrdf_load_stackoverflow) |
| CH (1) | CH564524A5 (enrdf_load_stackoverflow) |
| DD (1) | DD95238A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2115624A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2131750A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1377274A (enrdf_load_stackoverflow) |
| IT (1) | IT954404B (enrdf_load_stackoverflow) |
| NL (1) | NL7203765A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007031146A1 (de) | 2005-07-29 | 2007-03-22 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid |
| WO2018228984A1 (en) | 2017-06-14 | 2018-12-20 | Bayer Aktiengesellschaft | Process for preparing 3,4-dichloro-n-(2-cyanophenyl)-5-isothiazolecarboxamide |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10228732A1 (de) * | 2002-06-27 | 2004-01-15 | Bayer Cropscience Ag | Verfahren zur Herstellung von 3,4-Dichlor-N-(2-cyano-phenyl)-5-isothiazolcarboxamid |
| DE10228731A1 (de) * | 2002-06-27 | 2004-01-22 | Bayer Cropscience Ag | Verfahren zur Herstellung von 3,4-Dichlor-N-(2-cyanophenyl)-5-isothiazolcarboxamid |
-
1971
- 1971-03-31 DE DE19712115624 patent/DE2115624A1/de active Pending
-
1972
- 1972-03-02 CH CH307172A patent/CH564524A5/xx not_active IP Right Cessation
- 1972-03-21 NL NL7203765A patent/NL7203765A/xx unknown
- 1972-03-27 BE BE781275A patent/BE781275A/xx unknown
- 1972-03-29 DD DD16189672A patent/DD95238A5/xx unknown
- 1972-03-29 GB GB1470272A patent/GB1377274A/en not_active Expired
- 1972-03-30 IT IT4935772A patent/IT954404B/it active
- 1972-03-30 FR FR7211287A patent/FR2131750A5/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007031146A1 (de) | 2005-07-29 | 2007-03-22 | Bayer Cropscience Aktiengesellschaft | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyano-phenyl)-5-isothiazolcarboxamid |
| EP2573077A1 (de) | 2005-07-29 | 2013-03-27 | Bayer CropScience AG | Verfahren zur Herstellung von 3,4-Dichlor-N-(2-cyano-phenyl)-5-isothiazolcarboxamid |
| WO2018228984A1 (en) | 2017-06-14 | 2018-12-20 | Bayer Aktiengesellschaft | Process for preparing 3,4-dichloro-n-(2-cyanophenyl)-5-isothiazolecarboxamide |
| US11220487B2 (en) | 2017-06-14 | 2022-01-11 | Bayer Aktiengesellschaft | Process for preparing 3,4-dichloro-n-(2-cyanophenyl)-5-isothiazolecarboxamide |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2131750A5 (enrdf_load_stackoverflow) | 1972-11-10 |
| IT954404B (it) | 1973-08-30 |
| CH564524A5 (enrdf_load_stackoverflow) | 1975-07-31 |
| NL7203765A (enrdf_load_stackoverflow) | 1972-10-03 |
| BE781275A (fr) | 1972-09-27 |
| GB1377274A (en) | 1974-12-11 |
| DD95238A5 (enrdf_load_stackoverflow) | 1973-01-20 |
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