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Basic Information
CAS No.: 62666-20-0
Name: Progabide
Molecular Structure:
Molecular Structure of 62666-20-0 (Progabide)
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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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 .

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Questionable carcinogen with experimental neoplastigenic data reported. When heated to decomposition 4-(((4-CHLOROPHENYL)(5-FLUORO-2-HYDROXYPHENYL)METHYLENE)AMINO)-BUTANAMIDE(62666-20-0)  emits toxic vapors of NOx, F-, and, Cl-.