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Name	Progabide	EINECS	263-679-4
CAS No.	62666-20-0	Density	1.3g/cm³
PSA	75.68000	LogP	3.98790
Solubility	37.16mg/L(37 oC)	Melting Point	133-135°; mp 142.5° (Kaplan, J. Med. Chem.)
Formula	C17H16 Cl F N2 O2	Boiling Point	525.363°C at 760 mmHg
Molecular Weight	334.778	Flash Point	271.53°C
Transport Information	N/A	Appearance	N/A
Safety	Moderately toxic by ingestion and intraperitoneal routes. Questionable carcinogen with experimental neoplastigenic data reported. When heated to decomposition it emits toxic vapors of NO_x, F⁻, and, Cl⁻.	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	Gabren;Gabrene; Halogabide; Progabide; SL 76-002; SL 76002

Progabide Chemical Properties

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:

Progabide 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 SOCl₂gives 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 SOCl₂in 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.

Progabide 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 .

Progabide 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 NO_x, F^-, and, Cl^-.

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