GB2098210A - Process for the halogenation of N-(O,O'-dialkylphenyl)alaninates and homologues thereof - Google Patents
Process for the halogenation of N-(O,O'-dialkylphenyl)alaninates and homologues thereof Download PDFInfo
- Publication number
- GB2098210A GB2098210A GB8213005A GB8213005A GB2098210A GB 2098210 A GB2098210 A GB 2098210A GB 8213005 A GB8213005 A GB 8213005A GB 8213005 A GB8213005 A GB 8213005A GB 2098210 A GB2098210 A GB 2098210A
- Authority
- GB
- United Kingdom
- Prior art keywords
- process according
- compound
- general formula
- represent
- alkyl group
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000005658 halogenation reaction Methods 0.000 title abstract description 3
- 230000026030 halogenation Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000002841 Lewis acid Substances 0.000 claims abstract description 12
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 8
- QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- -1 Methyl N-(3-chloro-2,6-dimethylphenyl)alaninate Chemical compound 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-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
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- NEOYGRJJOGVQPO-UHFFFAOYSA-N methyl 2-(2,6-dimethylanilino)propanoate Chemical compound COC(=O)C(C)NC1=C(C)C=CC=C1C NEOYGRJJOGVQPO-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8109379A FR2505327A1 (fr) | 1981-05-08 | 1981-05-08 | Procede d'halogenation en meta de n-(o,o'-dialkyl phenyl) alaninates et homologues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2098210A true GB2098210A (en) | 1982-11-17 |
Family
ID=9258312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8213005A Withdrawn GB2098210A (en) | 1981-05-08 | 1982-05-05 | Process for the halogenation of N-(O,O'-dialkylphenyl)alaninates and homologues thereof |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE893117A (enrdf_load_stackoverflow) |
| DE (1) | DE3217029A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2505327A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2098210A (enrdf_load_stackoverflow) |
| IT (1) | IT1152114B (enrdf_load_stackoverflow) |
| LU (1) | LU84129A1 (enrdf_load_stackoverflow) |
| NL (1) | NL8201764A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4721797A (en) * | 1986-09-02 | 1988-01-26 | Ciba-Geigy Corporation | Process for the preparation of N-acyl-N-alkyl-2,6-dialkyl-3-chloroanilines |
| EP0310732A1 (de) * | 1987-10-09 | 1989-04-12 | Ciba-Geigy Ag | Verfahren zur Herstellung von N-Acyl-N-alkyl-2,6-dialkyl-3-chloranilinen |
| EP0347380A1 (de) * | 1988-06-14 | 1989-12-20 | Ciba-Geigy Ag | Verfahren zur Herstellung von 4-Bromanilin-hydrobromiden |
| AU597439B2 (en) * | 1986-09-02 | 1990-05-31 | Ciba-Geigy Ag | Process for the preparation of n-acyl-n-alkyl-2,6-dialkyl-3- chloroanilines |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1730729A (en) * | 1926-10-06 | 1929-10-08 | Gen Aniline Works Inc | Chlorsubstituted product of the 1-amino-2.4-dimethylbenzene and process of preparing it |
| US2813118A (en) * | 1953-07-16 | 1957-11-12 | American Cystoscope Makers Inc | X-ray contrast compounds |
| OA04979A (fr) * | 1974-04-09 | 1980-11-30 | Ciba Geigy | Nouveaux dérivés de l'aniline utiles comme agents microbicides et leur procédé de préparation. |
-
1981
- 1981-05-08 FR FR8109379A patent/FR2505327A1/fr active Granted
-
1982
- 1982-04-28 NL NL8201764A patent/NL8201764A/nl not_active Application Discontinuation
- 1982-05-04 IT IT21070/82A patent/IT1152114B/it active
- 1982-05-05 GB GB8213005A patent/GB2098210A/en not_active Withdrawn
- 1982-05-05 LU LU84129A patent/LU84129A1/fr unknown
- 1982-05-06 DE DE19823217029 patent/DE3217029A1/de not_active Withdrawn
- 1982-05-07 BE BE0/208038A patent/BE893117A/fr not_active IP Right Cessation
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4721797A (en) * | 1986-09-02 | 1988-01-26 | Ciba-Geigy Corporation | Process for the preparation of N-acyl-N-alkyl-2,6-dialkyl-3-chloroanilines |
| AU597439B2 (en) * | 1986-09-02 | 1990-05-31 | Ciba-Geigy Ag | Process for the preparation of n-acyl-n-alkyl-2,6-dialkyl-3- chloroanilines |
| EP0310732A1 (de) * | 1987-10-09 | 1989-04-12 | Ciba-Geigy Ag | Verfahren zur Herstellung von N-Acyl-N-alkyl-2,6-dialkyl-3-chloranilinen |
| EP0347380A1 (de) * | 1988-06-14 | 1989-12-20 | Ciba-Geigy Ag | Verfahren zur Herstellung von 4-Bromanilin-hydrobromiden |
| US4918230A (en) * | 1988-06-14 | 1990-04-17 | Ciba-Geigy Corporation | Process for the preparation 4-bromoaniline hydrobromides |
Also Published As
| Publication number | Publication date |
|---|---|
| BE893117A (fr) | 1982-11-08 |
| NL8201764A (nl) | 1982-12-01 |
| DE3217029A1 (de) | 1982-11-25 |
| FR2505327B1 (enrdf_load_stackoverflow) | 1984-08-10 |
| LU84129A1 (fr) | 1984-03-07 |
| FR2505327A1 (fr) | 1982-11-12 |
| IT1152114B (it) | 1986-12-31 |
| IT8221070A0 (it) | 1982-05-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |