p-Toluenesulfonic acid → 4-(1,3-Thiazol-2-yl)phenol

Reaction equation

[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[S:8])[NH2:7])=[CH:4][CH:3]=1.Br[CH2:12][CH:13](OC)OC.CC1C=CC(S(O)(=O)=O)=CC=1>CCO>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:8][CH:12]=[CH:13][N:7]=2)=[CH:4][CH:3]=1

Participants

Procedure

To a mixture of 4-hydroxybenzothioamide (30.64 g, 0.20 mol) and 2-bromo-1,1-dimethoxyethane (31.00 g, 0.20 mol) in EtOH (600 mL) was added 4-methylbenzenesulfonic acid (34.44 g, 0.20 mol) with stirring at rt. The reaction mixture was heated at 90° C. for 24 h, then cooled to rt and concentrated in vacuo. The mixture was diluted with H2O (200 mL), adjusted to pH 10 with saturated NaHCO3 aqueous solution and extracted with DCM (200 mL×3). The combined organic phases were concentrated in vacuo to give the title compound as s yellow solid (21.3 g, 60%).