Methanesulfonic Acid → 2-Methylcyclohexyl 5-amino-2-chlorobenzoate

반응식

CS(O)(=O)=O.[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13].[CH3:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1O>>[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:16])=[C:11]([CH:15]=1)[C:12]([O:14][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH:18]1[CH3:17])=[O:13]

참가 물질

반응물 3

HCID 6395Methanesulfonic Acid

HCID 114182-Methylcyclohexanol

HCID 378795-Amino-2-chlorobenzoic acid

생성물 1

HCID 189158082-Methylcyclohexyl 5-amino-2-chlorobenzoate수율 81.4%

실험 절차

Methanesulfonic acid (99%, 100 g, 1.0 mole) was added slowly to a stirred mixture of 5-amino-2-chlorobenzoic acid (85%, 100 g, 0.5 mole) in 2-methylcyclohexanol (200 g, 1.85 mole). The mixture was heated under reflux with stirring for 6 hours, then the excess 2-methylcyclohexanol was evaporated under reduced pressure. The residue was then dissolved in methylene chloride (800 ml), washed with water (300 ml), 5% sodium bicarbonate solution (300 ml), water (300 ml), dried (magnesium sulfate), and filtered. The solvent was then evaporated to give 109 g of 2-methylcyclohexyl 5-amino-2-chlorobenzoate as a light brown oil.