Dichloromethane → HCID 178516664, compound

Participants

Reaction Steps

To a solution of N-(4-chlorobenzyl-4-hydroxy-6-(hydroxymethyl)-3-quinolinecarbothioamide (0.082 g) from Preparation No. 46 in anhydrous dimethylformamide (4 mL) in a flame-dried flask is added dimethylaminopyridine (0.011 g), 2,4,6-collidine (0.035 mL), and methanesulfonyl chloride (0.017 mL). The reaction mixture is stirred at room temperature for 1 h after which time thin layer chromatography indicates starting material is nearly consumed. Morpholine (0.20 mL) is added in one portion. The reaction is stirred for 1.5 h and then poured into water. The aqueous solution is extracted 2× with CH2Cl2 and 2× with 3% MeOH:CH2Cl2. The organics are combined, dried over Na2SO4, filtered, and concentrated. Residual DMF is removed on the vacuum pump. The residue is dissolved in CH2Cl2 and hexanes was added to give a solid (starting material) which is filtered and dried. Upon allowing this filtrate to evaporate overnight, a second solid is obtained. This solid is dissolved in CH2Cl2 and adsorbed onto silica. Purification by chromatography (eluent CH2Cl2 (1 L), 1% MeOH:CH2Cl2 (1 L), 2% MeOH:CH2Cl2 (1 L) 2.5% MeOH:CH2Cl2 (1 L), 3% MeOH:CH2Cl2 (2 L)) affords N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarbothioamide (0.028 g) as a yellow solid.

Provenance & Evidence