Methanesulfonyl chloride → 6-(Chloromethyl)-2-(methylthio)benzo[d]thiazole

To a solution of (2-(methylthio)benzo[d]thiazol-6-yl)methanol (4.1 g, 19.4 mmol) from Step 2 of this Example and DIEA (3.26 g, 25.3 mmol) in CH2Cl2 (200 mL) was added methanesulfonyl chloride (2.88 g, 25.3 mmol) slowly at 0° C. The mixture was then treated with 2 drops of DMF and stirred at rt overnight. The mixture was quenched with 300 mL of saturated aq NaHCO3. The separated aqueous layer was extracted with CH2Cl2 (2×250 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure to give 6-(chloromethyl)-2-(methylthio)benzo[d]thiazole as a light brown solid (4.4 g, 99%). 1H NMR (300 MHz, DMSO-d6) δ 8.10 (d, J=1.5 Hz, 1H), 7.84 (d, J=8.5 Hz, 1H), 7.53 (dd, J=1.6, 8.4 Hz, 1H), 4.89 (s, 2H), 2.80 (s, 3H). LCMS (ESI) m/z 231 (M+H)+.

1. customslowly at 0° C
2. customThe mixture was quenched with 300 mL of saturated aq NaHCO3
3. extractionThe separated aqueous layer was extracted with CH2Cl2 (2×250 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated under reduced pressure

ORD record

ord-4ec1818519054bf48634e7eca3530ee8

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952058B2