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| CAS No.: | 62666-20-0 |
|---|---|
| Name: | Progabide |
| Molecular Structure: | |
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| Formula: | C17H16 Cl F N2 O2 |
| Molecular Weight: | 334.778 |
| Synonyms: | Gabren;Gabrene; Halogabide; Progabide; SL 76-002; SL 76002 |
| EINECS: | 263-679-4 |
| Density: | 1.3g/cm3 |
| Melting Point: | 133-135°; mp 142.5° (Kaplan, J. Med. Chem.) |
| Boiling Point: | 525.363°C at 760 mmHg |
| Flash Point: | 271.53°C |
| Solubility: | 37.16mg/L(37 oC) |
| Safety: | Moderately toxic by ingestion and intraperitoneal routes. Questionable carcinogen with experimental neoplastigenic data reported. When heated to decomposition it emits toxic vapors of NOx, F−, and, Cl−. |
| PSA: | 75.68000 |
| LogP: | 3.98790 |
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- Total:32 Page 1 of 1 1
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Chemistry
4-(((4-CHLOROPHENYL)(5-FLUORO-2-HYDROXYPHENYL)METHYLENE)AMINO)-BUTANAMIDE(62666-20-0) has the Molecular Formula of C17H16ClFN2O2 and the Molecular Weight of 334.80.
The structure:
Production
There are synthetic methods of 4-(((4-CHLOROPHENYL)(5-FLUORO-2-HYDROXYPHENYL)METHYLENE)AMINO)-BUTANAMIDE(62666-20-0).
Affording to 4-fluorophenyl-4-chlorobenzoate (IV),the reaction of p-chlorobenzoic acid (I) with SOCl2 gives p-chlorobenzoyl chloride (II), which is esterified with 4-fluorophenol (III)
The isomerization of (IV) with AlCl3 yields 4-chloro-2'-hydroxy-5'-fluorobenzophenone (V), which is condensed with 4-aminobutyric acid (VI) by means of sodium methoxide in ethanol giving 4-[[alpha-(p-chlorophenyl)-5-fluoro-2-hydroxybenzylidene]amino]butyric acid (VII).
The reaction of (VII) with SOCl2 in THF affords the corresponding acyl chloride (VIII).And then it treated with NH3.
By treatment with carbonyldiimidazole (A) and liquid NH3 in THF, converting the acid (VII) into its amide is an alternative way.
Toxicity Data With Reference
| 1. | orl-rat LD50:1350 mg/kg | LMSED6 L.E.R.S. Monograph Series. Laboratories d’Etudes et de Recherches Synthelabo Monograph Series. 3 (1985),203. | ||
| 2. | orl-mus LD50:1350 mg/kg | LMSED6 L.E.R.S. Monograph Series. Laboratories d’Etudes et de Recherches Synthelabo Monograph Series. 3 (1985),203. | ||
| 3. | ipr-mus LD50:900 mg/kg | USXXAM United States Patent Document. (Commissioner of Patents and Trademarks, Washington, DC 20231) #4094992 . |