CH378903A - Procédé de préparation d'un dérivé de la dichloracétanilide - Google Patents

Procédé de préparation d'un dérivé de la dichloracétanilide

Info

Publication number: CH378903A
Authority: CH; Switzerland
Prior art keywords: treatment; carried out; compound; dichloroacetylation; sub
Prior art date: 1957-11-08

Application number

CH6592258A

Other languages

English (en)

French (fr)

Inventor

Oxley Peter

William Bristow Norman

Stuart Nicholson John

Original Assignee

Boots Pure Drug Co Ltd

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.)

1957-11-08

Filing date

1958-11-07

Publication date

1964-06-30

1958-11-07 Application filed by Boots Pure Drug Co Ltd filed Critical Boots Pure Drug Co Ltd

1964-06-30 Publication of CH378903A publication Critical patent/CH378903A/fr

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
KJSVAEGLTPBKAA-UHFFFAOYSA-N 2,2-dichloro-n-phenylacetamide Chemical class ClC(Cl)C(=O)NC1=CC=CC=C1 KJSVAEGLTPBKAA-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 31
238000000034 method Methods 0.000 claims description 23
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
UFVLRHXFRXZBHS-UHFFFAOYSA-N 3,3,3-trichloro-2-hydroxypropanenitrile Chemical compound N#CC(O)C(Cl)(Cl)Cl UFVLRHXFRXZBHS-UHFFFAOYSA-N 0.000 claims description 4
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
STZZWJCGRKXEFF-UHFFFAOYSA-N Dichloroacetonitrile Chemical compound ClC(Cl)C#N STZZWJCGRKXEFF-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims description 2
230000011987 methylation Effects 0.000 claims description 2
238000007069 methylation reaction Methods 0.000 claims description 2
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims 2
IMTWOIBPRIRTLR-UHFFFAOYSA-N N-(3,6-dichloro-6-hydroxycyclohexa-2,4-dien-1-yl)acetamide Chemical compound ClC1(C(C=C(C=C1)Cl)NC(=O)C)O IMTWOIBPRIRTLR-UHFFFAOYSA-N 0.000 claims 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
229960005215 dichloroacetic acid Drugs 0.000 claims 1
238000011065 in-situ storage Methods 0.000 claims 1
239000012022 methylating agents‎ Substances 0.000 claims 1
239000011574 phosphorus Substances 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
239000000203 mixture Substances 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
WIWSJWAXUVHJBW-UHFFFAOYSA-N 2,2-dichloro-n-(4-hydroxyphenyl)acetamide Chemical compound OC1=CC=C(NC(=O)C(Cl)Cl)C=C1 WIWSJWAXUVHJBW-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
239000000243 solution Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
229940126062 Compound A Drugs 0.000 description 6
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
-1 dichloroacetyl group Chemical group 0.000 description 5
MOXTXYMFGOOPHY-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OC1=CC=C(C=C1)NC(C(Cl)Cl)=O Chemical compound C(C1=CC=CC=C1)(=O)OC1=CC=C(C=C1)NC(C(Cl)Cl)=O MOXTXYMFGOOPHY-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
LOCNFWNVXOMBSH-UHFFFAOYSA-N [4-[(2,2-dichloroacetyl)amino]phenyl] acetate Chemical compound CC(=O)OC1=CC=C(NC(=O)C(Cl)Cl)C=C1 LOCNFWNVXOMBSH-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000012265 solid product Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000003569 amebicidal effect Effects 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
229940049953 phenylacetate Drugs 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
IRLYGRLEBKCYPY-UHFFFAOYSA-M 2,5-dimethylbenzenesulfonate Chemical compound CC1=CC=C(C)C(S([O-])(=O)=O)=C1 IRLYGRLEBKCYPY-UHFFFAOYSA-M 0.000 description 1
BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
ZFIQGRISGKSVAG-UHFFFAOYSA-N 4-methylaminophenol Chemical compound CNC1=CC=C(O)C=C1 ZFIQGRISGKSVAG-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
208000004881 Amebiasis Diseases 0.000 description 1
206010001980 Amoebiasis Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
DGWFDTKFTGTOAF-UHFFFAOYSA-N P.Cl.Cl.Cl Chemical compound P.Cl.Cl.Cl DGWFDTKFTGTOAF-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000212342 Sium Species 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
229960002327 chloral hydrate Drugs 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloro-acetic acid amide Natural products NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229940087562 sodium acetate trihydrate Drugs 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulphite Substances [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms

Landscapes

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

CH6592258A 1957-11-08 1958-11-07 Procédé de préparation d'un dérivé de la dichloracétanilide CH378903A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3493457A GB850394A (en)	1957-11-08	1957-11-08	Process for the preparation of acetanilide derivatives

Publications (1)

Publication Number	Publication Date
CH378903A true CH378903A (fr)	1964-06-30

Family

ID=10371749

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6592258A CH378903A (fr)	1957-11-08	1958-11-07	Procédé de préparation d'un dérivé de la dichloracétanilide

Country Status (3)

Country	Link
CH (1)	CH378903A (da)
DK (2)	DK103295C (da)
GB (1)	GB850394A (da)

1957
- 1957-11-08 GB GB3493457A patent/GB850394A/en not_active Expired
1958
- 1958-11-05 DK DK349259A patent/DK103295C/da active
- 1958-11-05 DK DK399758A patent/DK103016C/da active
- 1958-11-07 CH CH6592258A patent/CH378903A/fr unknown

Also Published As

Publication number	Publication date
DK103016C (da)	1965-11-08
DK103295C (da)	1965-12-13
GB850394A (en)	1960-10-05

Publication	Publication Date	Title
CA1212380A (fr)	1986-10-07	Procede de preparation de nouveaux derives de thieno (2,3-b) pyrrole
CH378903A (fr)	1964-06-30	Procédé de préparation d'un dérivé de la dichloracétanilide
EP2173701A1 (fr)	2010-04-14	Procede de preparation du fenofibrate
JP2518014B2 (ja)	1996-07-24	α−置換酢酸の精製方法
CH432512A (fr)	1967-03-31	Procédé de préparation de stéroïdes 21-bromés
US2487004A (en)	1949-11-01	Preparation of lower alkyl (lower aliphatic acyl) aminocyanoacetates
FR2503152A1 (fr)	1982-10-08	Procede de preparation de l'a-(3,4,5-trimethoxybenzoylthio)-propionyl glycine
CH302799A (fr)	1954-10-31	Procédé de préparation d'un 1-nitrophényl-2-acylamido-propanediol-1,3.
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FR2918662A1 (fr)	2009-01-16	Procede de preparation du fenofibrate
CH307324A (fr)	1955-05-31	Procédé de préparation de l'amino-2-hydroxy-4-(chloro-4'-phényl)-5-éthyl-6-pyrimidine.
JPS60204772A (ja)	1985-10-16	イソオキサゾール誘導体の調製方法
CH222733A (fr)	1942-07-31	Procédé de préparation d'un dérivé de la para-amino-benzène-sulfamide.
CH298327A (fr)	1954-04-30	Procédé de préparation d'une forme thérapeutiquement active de la thréo-2-dichlorométhyl-4-hydroxyméthyl-5-p-nitrophényl-oxazoline-2.
CH302800A (fr)	1954-10-31	Procédé de préparation d'un 1-nitrophényl-2-acylamido-propanediol-1,3.
CH368164A (fr)	1963-03-31	Procédé pour la préparation de dérivés de l'étiocholane
JPS5946242A (ja)	1984-03-15	α−位に芳香族基を有するプロピオン酸及びそのエステルの製造方法
CH330478A (fr)	1958-06-15	Procédé de préparation de nouveaux thiodérivés de colchicéines
BE572479A (da)
CH222732A (fr)	1942-07-31	Procédé de préparation d'un dérivé de la para-amino-benzène-sulfamide.
FR2556341A1 (fr)	1985-06-14	Nouveau procede de preparation de l'acide hydroxy-3 methyl-3 glutarique
BE504827A (da)
CH265841A (fr)	1949-12-31	Procédé de préparation de l'ester éthylique de l'acide -(2-(4-carboxy)-thiazolidinyl)-phénacéturique.