Triethylamine → 2-Thiazolemethanol, 4-(2-chlorophenyl)-, 2-methanesulfonate

HRID 1944499Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH2:13][OH:14])[S:11][CH:12]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([O:14][CH2:13][C:10]1[S:11][CH:12]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:9]=1)(=[O:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

(4-(2-chlorophenyl)thiazol-2-yl)methanol 3 (0.41 g, 1.82 mmol) is dissolved in dichloromethane (25 mL). Triethylamine (0.50 mL, 3.56 mmol) is added and the solution is cooled to 0° C. Methanesulfonyl chloride (0.17 mL, 2.19 mmol) is added dropwise to the cooled solution, with stirring. The bath is removed and the mixture is stirred at room temperature for 3 h. Addition of water, extraction with DCM, drying over MgSO4 and concentration yielded (4-(2-chlorophenyl)thiazol-2-yl)methyl methanesulfonate 4 as an oil: 1H-NMR (400 MHz, CDCl3) δ=7.93 (s, 1H) 7.90 (dd, J=1.9, 7.7 Hz, 1H), 7.48 (dd, J=1.4, 7.7 Hz, 1H), 7.36 (ddd, J=1.4, 7.4, 7.6 Hz, 1H), 7.30 (ddd, J=1.9, 7.7, 7.5 Hz, 1H), 5.56 (s, 2H), 3.13 (s, 3H). MS calcd. for C11H11ClNO3S2 (M+H+) 304.0. found 303.9.

Workup

customThe bath is removed
stirringthe mixture is stirred at room temperature for 3 h
additionAddition of water, extraction with DCM
dry with materialdrying over MgSO4 and concentration

Sources & evidence

ORD record: ord-37dec4521b954992a5107469b52bdb9d
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394841B2

Reaction notes

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