CH339920A - Process for the preparation of dichloroacetanilide derivatives - Google Patents
Process for the preparation of dichloroacetanilide derivativesInfo
- Publication number
- CH339920A CH339920A CH339920DA CH339920A CH 339920 A CH339920 A CH 339920A CH 339920D A CH339920D A CH 339920DA CH 339920 A CH339920 A CH 339920A
- Authority
- CH
- Switzerland
- Prior art keywords
- dichloroacetanilide
- substituted
- hydroxy
- derivatives
- radical
- Prior art date
Links
- KJSVAEGLTPBKAA-UHFFFAOYSA-N 2,2-dichloro-n-phenylacetamide Chemical class ClC(Cl)C(=O)NC1=CC=CC=C1 KJSVAEGLTPBKAA-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- -1 N-substituted dichloroacetanilide Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006396 nitration reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000007787 solid Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940124323 amoebicide Drugs 0.000 description 1
- 239000000059 antiamebic agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation de dérivés de la dichloracétanilide La présente invention a pour objet un. procédé de préparation de dérivés de la dichloracétanilide, utili sables comme amibicides, de formule générale
EMI0001.0005
dans laquelle R représente un radical alcoyle ou aralcoyle d'au plus 8 atomes de carbone et Ar repré sente un radical phényle substitué par un ou plu sieurs groupes nitro et pouvant en outre être substi tué par un ou plusieurs groupes hydroxy, alcoxy,
aralcoxy, aryloxy, alcènoxy, alcoylènedioxy et - NRlR2, RI et R2 pouvant être les mêmes ou être différents et représentant chacun de l'hydrogène ou un groupe alcoyle, aralcoyle ou aryle.
Ce procédé est caractérisé en ce que l'on soumet la dichloracétanilide N - substituée correspondante à une nitration. Suivant l'utilisation prévue pour les composés obtenus, on peut ensuite réduire les grou pes nitro en groupes amino, par exemple au moyen de chlorure stanneux en présence d'acide chlorhydri que.
<I>Exemple 1</I> Pour préparer la dichloracet-4-hydroxy-N-méthyl- 3-nitroanilide, un mélange de 18 cc d'acide nitrique fumant et 60 cc d'acide acétique glacial est ajouté lentement à une suspension agitée de 15 g de di- chloracet - 4 - hydroxy-N-méthyl-anilide dans 60 cc d'acide acétique glacial. La température de réaction est maintenue au-dessous de 25,) C par refroidisse ment avec de l'eau.
Lorsque l'adjonction est terminée, la solution brun clair résultante est agitée pendant encore une demi-heure et est versée dans un grand excès d'un mélange de glace et d'eau. Le précipité qui se sépare est recueilli par filtration, lavé avec une petite quantité d'eau et cristallisé deux fois à partir de portions de 40 cc d'alcool. On obtient ainsi la dichloracet-4-hydroxy-N-méthyl-3-nitroamlide sous forme d'un solide cristallin ayant un point de fusion de 111o C.
(Trouvé: N, 10,2. Calculé pour C,H804N±12 N, 10,0 a/0).
<I>Exemple 2</I> Pour préparer la dichloracet-4-hydroxy-N-méthyl- 3,5-dinitroanilide, 20 g de dichloracet-4-hydroxy-N- méthyl-3-nitroanilide (préparée comme décrit à l'exemple 1), sont ajoutés lentement à 200 cc d'acide nitrique fumant en agitant et refroidissant pour main- tenir 1a température de la réaction au-dessous de 50 C.
Quand l'adjonction est terminée, la solution ainsi ob tenue est agitée à 0 - 5o C pendant une heure, puis elle est versée dans un grand excès d'un mélange de glace et d'eau. Le précipité qui se sépare est isolé par filtration puis est cristallisé dans de l'alcool aqueux. On obtient un solide cristallin jaune ayant un point de fusion de 129-1301, C.
La structure cris- talline de ce solide change quand on le maintient à la température ordinaire pendant quelques jours, en donnant un solide stable à point de fusion plus élevé. On obtient ainsi la dichloracet-4-hydroxy-N-méthyl- 3,5-dinitroanilide sous forme d'un solide cristallin ayant un point de fusion de 144 - 146o C.
(Trouvé: N, 13,0. Calculé pour CqH7061s#102 N, 13,0 ()/a).
A process for preparing dichloroacetanilide derivatives The present invention relates to a. process for the preparation of dichloroacetanilide derivatives, usable as amebicides, of general formula
EMI0001.0005
in which R represents an alkyl or aralkyl radical of at most 8 carbon atoms and Ar represents a phenyl radical substituted by one or more nitro groups and which may also be substituted by one or more hydroxy or alkoxy groups,
aralkoxy, aryloxy, alkenoxy, alkylenedioxy and - NRlR2, RI and R2 may be the same or be different and each represents hydrogen or an alkyl, aralkyl or aryl group.
This process is characterized in that the corresponding N - substituted dichloroacetanilide is subjected to nitration. Depending on the intended use of the compounds obtained, the nitro groups can then be reduced to amino groups, for example by means of stannous chloride in the presence of hydrochloric acid.
<I> Example 1 </I> To prepare dichloroacet-4-hydroxy-N-methyl-3-nitroanilide, a mixture of 18 cc of fuming nitric acid and 60 cc of glacial acetic acid is slowly added to a suspension stirred 15 g of dichloroacet - 4 - hydroxy-N-methyl-anilide in 60 cc of glacial acetic acid. The reaction temperature is kept below 25 ° C by cooling with water.
When the addition is complete, the resulting light brown solution is stirred for a further half an hour and is poured into a large excess of a mixture of ice and water. The precipitate which separates is collected by filtration, washed with a small amount of water and crystallized twice from 40 cc portions of alcohol. This gives dichloroacet-4-hydroxy-N-methyl-3-nitroamlide in the form of a crystalline solid having a melting point of 111o C.
(Found: N, 10.2. Calculated for C, H804N ± 12 N, 10.0 a / 0).
<I> Example 2 </I> To prepare dichloracet-4-hydroxy-N-methyl-3,5-dinitroanilide, 20 g of dichloracet-4-hydroxy-N-methyl-3-nitroanilide (prepared as described in l (Example 1), are slowly added to 200 cc of fuming nitric acid with stirring and cooling to keep the reaction temperature below 50 C.
When the addition is complete, the solution thus obtained is stirred at 0 - 5o C for one hour, then it is poured into a large excess of a mixture of ice and water. The precipitate which separates is isolated by filtration and then crystallized from aqueous alcohol. A yellow crystalline solid is obtained having a melting point of 129-1301, C.
The crystalline structure of this solid changes when kept at room temperature for a few days, giving a stable solid with a higher melting point. In this way dichloroacet-4-hydroxy-N-methyl-3,5-dinitroanilide is obtained in the form of a crystalline solid having a melting point of 144 - 146o C.
(Found: N, 13.0. Calculated for CqH7061s # 102 N, 13.0 () / a).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB339920X | 1955-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH339920A true CH339920A (en) | 1959-07-31 |
Family
ID=10359993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH339920D CH339920A (en) | 1955-03-24 | 1955-07-22 | Process for the preparation of dichloroacetanilide derivatives |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH339920A (en) |
-
1955
- 1955-07-22 CH CH339920D patent/CH339920A/en unknown
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