PL114555B1 - Process for preparing secondary amides of dichloroacetic acid - Google Patents

Process for preparing secondary amides of dichloroacetic acid Download PDF

Info

Publication number: PL114555B1
Authority: PL; Poland
Prior art keywords: dichloroacetic acid; acid; carbon atoms; general formula; mixture
Prior art date: 1976-12-23

Application number

PL20319977A

Other languages

English (en)

Polish (pl)

Other versions

PL203199A1 (pl

Inventor

Attila Kistamas

Laszlo Majoros

Ferenc Jurak

Gabor Fried

Istvan Orban

Jozsef Halmos

Gyorgy Mihalyi

Istvan Kovacs

Csaba Kiss

Laszlo Gora

Original Assignee

Egyt Gyogyszervegyeszeti Gyarhu

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.)

1976-12-23

Filing date

1977-12-21

Publication date

1981-02-28

1977-12-21 Application filed by Egyt Gyogyszervegyeszeti Gyarhu filed Critical Egyt Gyogyszervegyeszeti Gyarhu

1978-09-11 Publication of PL203199A1 publication Critical patent/PL203199A1/xx

1981-02-28 Publication of PL114555B1 publication Critical patent/PL114555B1/pl

Links

JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 title claims description 30
229960005215 dichloroacetic acid Drugs 0.000 title claims description 15
238000004519 manufacturing process Methods 0.000 title description 2
150000003334 secondary amides Chemical class 0.000 title 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
238000000034 method Methods 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 9
WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical group NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
150000004703 alkoxides Chemical class 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
125000005936 piperidyl group Chemical group 0.000 claims description 3
239000000203 mixture Substances 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000002253 acid Substances 0.000 description 11
150000001412 amines Chemical class 0.000 description 10
HKMLRUAPIDAGIE-UHFFFAOYSA-N methyl 2,2-dichloroacetate Chemical compound COC(=O)C(Cl)Cl HKMLRUAPIDAGIE-UHFFFAOYSA-N 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
239000000047 product Substances 0.000 description 9
238000005917 acylation reaction Methods 0.000 description 8
230000010933 acylation Effects 0.000 description 7
-1 aliphatic amines Chemical class 0.000 description 7
150000004702 methyl esters Chemical class 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 6
238000004821 distillation Methods 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 5
239000012071 phase Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 2
GZEXALCIMJQLRM-UHFFFAOYSA-N 2,2-dichloro-n-hexyl-n-methylacetamide Chemical compound CCCCCCN(C)C(=O)C(Cl)Cl GZEXALCIMJQLRM-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
230000021736 acetylation Effects 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
229940106681 chloroacetic acid Drugs 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 2
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
150000002561 ketenes Chemical class 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
OYWSDPCOGRWYGN-UHFFFAOYSA-N 1,1-dichloro-5-(propylamino)pentan-2-one Chemical compound CCCNCCCC(=O)C(Cl)Cl OYWSDPCOGRWYGN-UHFFFAOYSA-N 0.000 description 1
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical class ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
XQDMHNNCUPFGLB-UHFFFAOYSA-N 2,2-dichlorobutanamide Chemical compound CCC(Cl)(Cl)C(N)=O XQDMHNNCUPFGLB-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
238000010934 O-alkylation reaction Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
238000003833 Wallach reaction Methods 0.000 description 1
VXJPCEOTZNHHOA-UHFFFAOYSA-N [K].OC Chemical compound [K].OC VXJPCEOTZNHHOA-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000000729 antidote Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000000383 hazardous chemical Substances 0.000 description 1
231100000206 health hazard Toxicity 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
TZNULHNPXDZANP-UHFFFAOYSA-N magnesium;methanol Chemical compound [Mg].OC TZNULHNPXDZANP-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
JVJBRAUSPKGXBP-UHFFFAOYSA-N n-benzyl-2,2-dichloro-n-methylacetamide Chemical compound ClC(Cl)C(=O)N(C)CC1=CC=CC=C1 JVJBRAUSPKGXBP-UHFFFAOYSA-N 0.000 description 1
NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000000053 physical method Methods 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

PL20319977A 1976-12-23 1977-12-21 Process for preparing secondary amides of dichloroacetic acid PL114555B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUEE002466 HU176376B (en)	1976-12-23	1976-12-23	Process for producing sec amides of dichloroacetic acide

Publications (2)

Publication Number	Publication Date
PL203199A1 PL203199A1 (pl)	1978-09-11
PL114555B1 true PL114555B1 (en)	1981-02-28

Family

ID=10995711

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL20319977A PL114555B1 (en)	1976-12-23	1977-12-21	Process for preparing secondary amides of dichloroacetic acid

Country Status (12)

Country	Link
JP (1)	JPS53111012A (de)
AT (1)	AT353767B (de)
BE (1)	BE861870A (de)
BG (1)	BG28569A3 (de)
CH (1)	CH631434A5 (de)
DD (1)	DD133792A5 (de)
DE (1)	DE2757813A1 (de)
FR (1)	FR2375189A1 (de)
HU (1)	HU176376B (de)
PL (1)	PL114555B1 (de)
SU (1)	SU884562A3 (de)
YU (1)	YU40824B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3003898A1 (de) *	1980-02-02	1981-08-13	Dynamit Nobel Ag, 5210 Troisdorf	Verfahren zur acylierung von aminocarbonsaeuren

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR926115A (fr) *	1943-09-13	1947-09-23	Lankro Chem Ltd	Procédé d'amidation des esters
US3462486A (en) *	1966-12-28	1969-08-19	Gulf Oil Corp	Method for preparing 3',4'-dichloro-cyclopropanecarboxanilide

1976
- 1976-12-23 HU HUEE002466 patent/HU176376B/hu not_active IP Right Cessation
1977
- 1977-12-02 CH CH1475577A patent/CH631434A5/de not_active IP Right Cessation
- 1977-12-06 DD DD20242677A patent/DD133792A5/de unknown
- 1977-12-09 AT AT881177A patent/AT353767B/de not_active IP Right Cessation
- 1977-12-12 BG BG038011A patent/BG28569A3/xx unknown
- 1977-12-14 FR FR7737631A patent/FR2375189A1/fr active Granted
- 1977-12-15 BE BE1008585A patent/BE861870A/xx not_active IP Right Cessation
- 1977-12-19 SU SU772556898A patent/SU884562A3/ru active
- 1977-12-21 PL PL20319977A patent/PL114555B1/pl unknown
- 1977-12-22 YU YU305477A patent/YU40824B/xx unknown
- 1977-12-23 JP JP15456377A patent/JPS53111012A/ja active Pending
- 1977-12-23 DE DE19772757813 patent/DE2757813A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
SU884562A3 (ru)	1981-11-23
FR2375189A1 (fr)	1978-07-21
DD133792A5 (de)	1979-01-24
CH631434A5 (en)	1982-08-13
ATA881177A (de)	1979-05-15
BE861870A (fr)	1978-06-15
AT353767B (de)	1979-12-10
YU40824B (en)	1986-06-30
YU305477A (en)	1982-08-31
DE2757813A1 (de)	1978-06-29
FR2375189B1 (de)	1983-10-28
PL203199A1 (pl)	1978-09-11
HU176376B (en)	1981-02-28
JPS53111012A (en)	1978-09-28
BG28569A3 (bg)	1980-05-15

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