Methanesulfonyl chloride → 3-(4-Phenylthiazol-2-yl)propyl methanesulfonate
Reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][CH2:14][OH:15])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[CH3:16][S:17]([O:15][CH2:14][CH2:13][CH2:12][C:9]1[S:10][CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1)(=[O:19])=[O:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-(4-phenylthiazol-2-yl)propan-1-ol (0.4 g, 1.82 mmol) in dry pyridine (8 mL) was cooled to 0° C. and methanesulfonyl chloride (0.43 mL, 5.47 mmol) was added dropwise. The reaction mixture was allowed to warm up to room temperature, stirred for 1 h, and quenched with ice water. The organic product was extracted with EtOAc and organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 3-(4-phenylthiazol-2-yl)propyl methanesulfonate (0.4 g, yield 74%) as a pale yellow liquid, which was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 7.90-7.87 (m, 2H), 7.46-7.40 (m, 2H), 7.37-7.31 (m, 2H), 4.42-4.38 (t, J=6.1 Hz, 2H), 3.24-3.19 (t, J=7.2 Hz, 2H), 3.04 (s, 3H), 2.39-2.30 (m, 2H). MS (ESI) m/z: Calculated for C13H15NO3S2: 297.05. found: 298.0 (M+H)+.