IL105164A - Preparation of a history of N-phenyl-N-methoxyacetyl-LD-alanine methyl ester - Google Patents

Preparation of a history of N-phenyl-N-methoxyacetyl-LD-alanine methyl ester

Info

Publication number: IL105164A
Authority: IL; Israel
Prior art keywords: methoxyacetyl; methyl; preparation; phenyl; methyl ester
Prior art date: 1992-03-27

Application number

IL10516493A

Other languages

English (en)

Hebrew (he)

Other versions

IL105164A0 (en

Original Assignee

Nitrokemia Ipartelepek

Priority date (The priority date 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 date listed.)

1992-03-27

Filing date

1993-03-25

Publication date

1998-09-24

1993-03-25 Application filed by Nitrokemia Ipartelepek filed Critical Nitrokemia Ipartelepek

1993-07-08 Publication of IL105164A0 publication Critical patent/IL105164A0/xx

1998-09-24 Publication of IL105164A publication Critical patent/IL105164A/en

Links

238000002360 preparation method Methods 0.000 title claims abstract description 13
KIJUZUWPPGRWBA-UHFFFAOYSA-N methyl 2-(n-(2-methoxyacetyl)anilino)propanoate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=CC=CC=C1 KIJUZUWPPGRWBA-UHFFFAOYSA-N 0.000 title claims abstract description 4
238000000034 method Methods 0.000 claims abstract description 29
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
229910052751 metal Inorganic materials 0.000 claims abstract description 9
239000002184 metal Substances 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 7
150000004703 alkoxides Chemical class 0.000 claims abstract 3
238000002955 isolation Methods 0.000 claims abstract 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 25
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 12
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
239000008096 xylene Substances 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 2
230000008034 disappearance Effects 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 14
239000000047 product Substances 0.000 description 14
239000012071 phase Substances 0.000 description 13
239000005807 Metalaxyl Substances 0.000 description 12
ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
239000002253 acid Substances 0.000 description 8
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
230000029936 alkylation Effects 0.000 description 7
238000005804 alkylation reaction Methods 0.000 description 7
239000011230 binding agent Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
230000000855 fungicidal effect Effects 0.000 description 6
238000009835 boiling Methods 0.000 description 5
238000004821 distillation Methods 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000002168 alkylating agent Substances 0.000 description 4
229940100198 alkylating agent Drugs 0.000 description 4
238000007086 side reaction Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
HCLNRFWBRJXGNA-UHFFFAOYSA-N n-methoxy-n-phenylacetamide Chemical compound CON(C(C)=O)C1=CC=CC=C1 HCLNRFWBRJXGNA-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241001281803 Plasmopara viticola Species 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
-1 methoxy acet Chemical compound 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
OXXYGGDIKKXTFB-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-methoxyacetamide Chemical compound COCC(=O)NC1=C(C)C=CC=C1C OXXYGGDIKKXTFB-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000004064 recycling Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000002699 waste material Substances 0.000 description 2
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
101100162703 Caenorhabditis elegans ani-1 gene Proteins 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
241001223281 Peronospora Species 0.000 description 1
235000002492 Rungia klossii Nutrition 0.000 description 1
244000117054 Rungia klossii Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
HOSOTBRBJDEJIK-UHFFFAOYSA-N [Na].CON(C1=C(C=CC=C1C)C)C(C)=O Chemical compound [Na].CON(C1=C(C=CC=C1C)C)C(C)=O HOSOTBRBJDEJIK-UHFFFAOYSA-N 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
UCKZQZDVQVFOHP-UHFFFAOYSA-N bromo propanoate Chemical compound CCC(=O)OBr UCKZQZDVQVFOHP-UHFFFAOYSA-N 0.000 description 1
VIRPUNZTLGQDDV-UHFFFAOYSA-N chloro propanoate Chemical compound CCC(=O)OCl VIRPUNZTLGQDDV-UHFFFAOYSA-N 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
230000002542 deteriorative effect Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000010815 organic waste Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/08—Preparation of carboxylic acid amides from amides by reaction at nitrogen atoms of carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/68—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom and to a carbon atom of a six-membered aromatic ring wherein at least one ortho-hydrogen atom has been replaced

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL10516493A 1992-03-27 1993-03-25 Preparation of a history of N-phenyl-N-methoxyacetyl-LD-alanine methyl ester IL105164A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU9201020A HU208806B (en)	1992-03-27	1992-03-27	Improved method for producing n-phenyl-n-methoxi-acetyl-d1-alanine-methylesther derivatives

Publications (2)

Publication Number	Publication Date
IL105164A0 IL105164A0 (en)	1993-07-08
IL105164A true IL105164A (en)	1998-09-24

Family

ID=10981622

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10516493A IL105164A (en)	1992-03-27	1993-03-25	Preparation of a history of N-phenyl-N-methoxyacetyl-LD-alanine methyl ester

Country Status (12)

Country	Link
US (1)	US5639905A (de)
EP (1)	EP0643687B1 (de)
AT (1)	ATE167178T1 (de)
BR (1)	BR9306152A (de)
CA (1)	CA2132538A1 (de)
DE (1)	DE69319113T2 (de)
ES (1)	ES2121080T3 (de)
HU (1)	HU208806B (de)
IL (1)	IL105164A (de)
MX (1)	MX9301676A (de)
RO (1)	RO113241B1 (de)
WO (1)	WO1993020041A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN116514677B (zh) *	2023-05-05	2024-11-15	上海农帆生物科技有限公司	一种精甲霜灵的制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3048626A (en) *	1960-12-05	1962-08-07	Mallinckrodt Chemical Works	N-(2, 4, 6-triiodophenyl) aceturic acid and sodium salt
DE2212268C3 (de) *	1971-03-15	1979-09-13	Sumitomo Chemical Co., Ltd., Osaka (Japan)	N-Halogenacetylanilinoessigsäureester, Verfahren zu deren Herstellung und diese enthaltende herbicide Massen
CH607888A5 (en) *	1975-03-14	1978-12-15	Ciba Geigy Ag	Microbicides
CH639643A5 (en) *	1979-03-21	1983-11-30	Ciba Geigy Ag	Pesticides
US4377587A (en) *	1980-07-25	1983-03-22	Ciba-Geigy Corporation	Arylamine derivatives and use thereof as microbicides
HU202481B (en) *	1989-04-19	1991-03-28	Nitrokemia Ipartelepek	Process for producing n-phenyl-n-(methoxyacetyl)-dl-alanine methyl ester derivatives

1992
- 1992-03-27 HU HU9201020A patent/HU208806B/hu not_active IP Right Cessation
1993
- 1993-03-24 ES ES93908054T patent/ES2121080T3/es not_active Expired - Lifetime
- 1993-03-24 BR BR9306152A patent/BR9306152A/pt not_active Application Discontinuation
- 1993-03-24 AT AT93908054T patent/ATE167178T1/de active
- 1993-03-24 DE DE69319113T patent/DE69319113T2/de not_active Expired - Fee Related
- 1993-03-24 EP EP93908054A patent/EP0643687B1/de not_active Expired - Lifetime
- 1993-03-24 RO RO94-01582A patent/RO113241B1/ro unknown
- 1993-03-24 WO PCT/HU1993/000017 patent/WO1993020041A1/en not_active Ceased
- 1993-03-24 CA CA002132538A patent/CA2132538A1/en not_active Abandoned
- 1993-03-25 IL IL10516493A patent/IL105164A/en not_active IP Right Cessation
- 1993-03-25 MX MX9301676A patent/MX9301676A/es not_active IP Right Cessation
1994
- 1994-09-13 US US08/368,271 patent/US5639905A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
WO1993020041A1 (en)	1993-10-14
BR9306152A (pt)	1998-01-13
ATE167178T1 (de)	1998-06-15
DE69319113D1 (de)	1998-07-16
DE69319113T2 (de)	1998-12-03
CA2132538A1 (en)	1993-10-14
US5639905A (en)	1997-06-17
HU208806B (en)	1994-01-28
IL105164A0 (en)	1993-07-08
ES2121080T3 (es)	1998-11-16
MX9301676A (es)	1993-09-01
HU9201020D0 (en)	1992-06-29
EP0643687A1 (de)	1995-03-22
EP0643687B1 (de)	1998-06-10
RO113241B1 (ro)	1998-05-29

Legal Events

Date	Code	Title
1999-01-26	FF	Patent granted
1999-07-14	KB	Patent renewed
2000-02-17	RH	Patent void

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