Methanol → Methyl 3-amino-2-methyl-4-methylsulfanylbenzoate

Reaction equation

[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:8]=[CH:9][C:10]=1[S:11][CH3:12])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.O.[CH3:20]O>>[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:8]=[CH:9][C:10]=1[S:11][CH3:12])[C:5]([O:7][CH3:20])=[O:6]

Participants

Reactant 4

HCID 887Methanol

HCID 962Water

HCID 1118Sulfuric Acid

HCID 186160433-Amino-2-methyl-4-methylsulfanylbenzoic acid

Product 1

HCID 18616042Methyl 3-amino-2-methyl-4-methylsulfanylbenzoate

Conditions

Temperature: 60 °C

Procedure

2 g of 3-amino-2-methyl-4-methylsulfanylbenzoic acid (0.01 mol) were dissolved in 20 ml of methanol and admixed with 2.0 g of conc. sulfuric acid, and the mixture was heated at 60° C. for 2 h. After cooling, the reaction mixture was poured into water, neutralized and extracted with ethyl acetate. After washing and drying, the solvent was removed.