Stearoyl chloride → HCID 9890245, compound

Reaction equation

C(N(CC)CC)C.[CH3:8][N:9]([CH3:22])[CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:15]([NH2:21])=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1.[C:23](Cl)(=O)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>ClCCl>[CH2:39]([C:40]1[N:13]([CH2:12][CH2:11][CH2:10][N:9]([CH3:8])[CH3:22])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[N:21]=1)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23]

Participants

Procedure

Triethylamine (0.557 g) was added to a solution containing N1-[3-(dimethylamino)propyl]4-methyl-1,2-benzenediamine (1.037 g) in dichloromethane (5 ml), and then a solution containing stearoyl chloride (1.515 g) in dichloromethane (5 mnl) was added thereto while being cooled with ice. After being stirred for 4.5 hours at room temperature, the reaction mixture was diluted with dichloromethane, washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. Concentrated hydrochloric acid (3.5 ml) was added to a solution containing the residue (1.97 g) in ethanol (20 ml). After being stiffed for 5.5 hours at 90° C., the reaction mixture was concentrated. The residue, with chloroform added thereto, was washed with 0.5N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue (1.03 g) was purified by silica gel column chromatography (silica gel 30 g, chloroform:methanol=50:1-1:1), thereby yielding the entitled compound (0.714 g) as pale yellow solid.