Potassium Carbonate → 6-(4-Methylthiazol-2-yl)thiohexan-1-ol

Reaction equation

[SH:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:7][C:5]1[N:6]=[C:2]([S:1][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[S:3][CH:4]=1

Participants

Procedure

The mixture of 2-mercapto-4-methylthiazole (2.62 g, 0.02 mol), 6-bromo-1-hexanol (3.62 g, 0.02 mol), potassium carbonate (2.76 g, 0.02 mol) and acetone (50 mL) was refluxed for 14 h. After cooling, the mixture was filtered and the filtrate was evaporated. The residual oil was purified by elution from a silica gel column using ethylacetate-methanol (99:1, v./v) as eluant to give 6-(4-methylthiazol-2-yl)thiohexan-1-ol (29) (99%) as a yellowish oil. IR (neat) 3608 (OH)cm-1 ; NMR (CDCl3) 1.25-2.10 (m, 8H, (CH2)4), 2.38 (S, 3H, Me-Het), 3.18 (t, J=9 Hz, 2H, CH2 --S), 3 65 (t, J=9 Hz, 2H, CH2 --O), 6.75 (S, 1H, H-Het). Analysis found: C, 51.98; H, 7.49; N, 5.92; S, 27.65. Required: C, 51.90; H, 7.40; N, 6.08; S, 27.71 (C10H17NOS2). ##STR11##