methyl thiocyanate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 4-(4-n-octylphenyl)phenol (2.82 g) in 1,2-dichloroethane (40 ml) is added a 2M borone trichloride - 1,2-dichloroethane solution (6 ml) under ice cooling, and thereto are further added methyl thiocyanate (0.82 ml) and aluminum chloride (1.33 g). The mixture is stirred at room temperature until aluminum chloride is dissolved, and is further stirred at 80° C. for 3 hours. After cooling, 4N aqueous sodium hydroxide solution (33 ml) is added to the reaction mixture, and the mixture is stirred at 75°-80° C. for 30 minutes. After cooling, the reaction mixture is washed with methylene chloride, and the aqueous layer is adjusted to pH 2 with 6N hydrochloric acid and then extracted with ether. The extract is dried and then ether is distilled off under reduced pressure. The crude crystal thus obtained is purified by silica gel column chromatography to give 4-(4-n-octylphenyl)-2-cyanophenol (2.03 g) of the following formula: ##STR32## is added a 2M is dissolved After cooling the mixture is stirred at 75°-80° C. for 30 minutes After cooling the reaction mixture is washed with methylene chloride extracted with ether The extract is dried ether is distilled off under reduced pressure The crude crystal thus obtained is purified by silica gel column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-4,5-Dihydro-2-(5-fluoro-2-hydroxyphenyl)-4-thiazolecarboxylic acid (5′-fluorodesazadesmethylDFT, 29a) is prepared from the cyclization of D-cysteine onto 5-fluoro-2-hydroxybenzonitrile in slightly acidic buffer. The aromatic precursor could be made by direct cyanation of p-fluorophenol using methyl thiocyanate, aluminum chloride, and boron trichloride in ethylene dichloride followed by heating in aqueous base (Adachi et al., Syn. Commun. 20:71-84 (1990)). by heating in aqueous base (Adachi et al., Syn. Commun. 20:71-84 (1990))

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (S)-4,5-Dihydro-2-(5-fluoro-2-hydroxyphenyl)-4-thiazolecarboxylic acid (5′-fluorodesazadesmethylDFT, 29a) is prepared from the cyclization of D-cysteine onto 5-fluoro-2-hydroxybenzonitrile in slightly acidic buffer. The aromatic precursor could be made by direct cyanation of p-fluorophenol using methyl thiocyanate, aluminum chloride, and boron trichloride in ethylene dichloride followed by heating in aqueous base (Adachi et al., Syn. Commun. 20:71-84 (1990)). by heating in aqueous base (Adachi et al., Syn. Commun. 20:71-84 (1990))