FR2505327A1 - Procede d'halogenation en meta de n-(o,o'-dialkyl phenyl) alaninates et homologues - Google Patents
Procede d'halogenation en meta de n-(o,o'-dialkyl phenyl) alaninates et homologues Download PDFInfo
- Publication number
- FR2505327A1 FR2505327A1 FR8109379A FR8109379A FR2505327A1 FR 2505327 A1 FR2505327 A1 FR 2505327A1 FR 8109379 A FR8109379 A FR 8109379A FR 8109379 A FR8109379 A FR 8109379A FR 2505327 A1 FR2505327 A1 FR 2505327A1
- Authority
- FR
- France
- Prior art keywords
- formula
- compound
- lewis acid
- halogen
- compounds
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 230000026030 halogenation Effects 0.000 title abstract description 4
- 238000005658 halogenation reaction Methods 0.000 title abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title abstract 2
- 239000002841 Lewis acid Substances 0.000 claims abstract description 10
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- -1 compound compound Chemical class 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 241001331845 Equus asinus x caballus Species 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000047 product Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 108010001496 Galectin 2 Proteins 0.000 description 1
- 102100021735 Galectin-2 Human genes 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
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Polymers 0.000 description 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 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
- 125000000524 functional group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- DWKPPFQULDPWHX-VKHMYHEASA-N l-alanyl ester Chemical compound COC(=O)[C@H](C)N DWKPPFQULDPWHX-VKHMYHEASA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
Priority Applications (7)
| 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 |
| NL8201764A NL8201764A (nl) | 1981-05-08 | 1982-04-28 | Werkwijze ter bereiding van n-(m-halogeenfenyl)aminozuuresters. |
| IT21070/82A IT1152114B (it) | 1981-05-08 | 1982-05-04 | Procedimento di alogenazione di n-(0,0'-dialchilfenil) alaninati e omologhi |
| GB8213005A GB2098210A (en) | 1981-05-08 | 1982-05-05 | Process for the halogenation of N-(O,O'-dialkylphenyl)alaninates and homologues thereof |
| LU84129A LU84129A1 (fr) | 1981-05-08 | 1982-05-05 | Procede d'halogenation en meta de n-(o,o'-dialkyl phenyl)alaninates et homologues |
| DE19823217029 DE3217029A1 (de) | 1981-05-08 | 1982-05-06 | Verfahren zur herstellung von n-(m-halogenphenyl)-(alpha)-aminosaeureestern |
| BE0/208038A BE893117A (fr) | 1981-05-08 | 1982-05-07 | Procede d'halogenation de n-(0,0'-dialkyl phenyl) alaniates et homologues) |
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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2505327A1 true FR2505327A1 (fr) | 1982-11-12 |
| FR2505327B1 FR2505327B1 (enrdf_load_stackoverflow) | 1984-08-10 |
Family
ID=9258312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8109379A Granted FR2505327A1 (fr) | 1981-05-08 | 1981-05-08 | Procede d'halogenation en meta de n-(o,o'-dialkyl phenyl) alaninates et homologues |
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) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0310732B1 (de) * | 1987-10-09 | 1992-03-11 | Ciba-Geigy Ag | Verfahren zur Herstellung von N-Acyl-N-alkyl-2,6-dialkyl-3-chloranilinen |
| JPH01106850A (ja) * | 1986-09-02 | 1989-04-24 | Ciba Geigy Ag | Ｎ−アシル−ｎ−アルキル−２，６−ジアルキル−３−クロロアニリンの製造方法 |
| 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 |
| US4918230A (en) * | 1988-06-14 | 1990-04-17 | Ciba-Geigy Corporation | Process for the preparation 4-bromoaniline hydrobromides |
Citations (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 |
| FR2267042A1 (enrdf_load_stackoverflow) * | 1974-04-09 | 1975-11-07 | Ciba Geigy Ag |
-
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
Patent Citations (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 |
| FR2267042A1 (enrdf_load_stackoverflow) * | 1974-04-09 | 1975-11-07 | Ciba Geigy Ag |
Non-Patent Citations (2)
| Title |
|---|
| CA1964 * |
| EXBK/62 * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2098210A (en) | 1982-11-17 |
| 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 |
| IT1152114B (it) | 1986-12-31 |
| IT8221070A0 (it) | 1982-05-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |