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

To a stirred mixture of (2-(methylthio)benzo[d]thiazol-6-yl)methanol (1.05 g, 5 mmol) from Step 3 of this Example and DIEA (1.3 mL, 7.5 mmol) in anhydrous CH2Cl2 (20 mL) under argon at −10° C. was added dropwise a solution of methanesulfonyl chloride (0.6 g, 5.5 mmol) in CH2Cl2 (10 mL). The mixture was allowed to warm to rt and stirred for 3 h. Additional methanesulfonyl chloride (190 mg, 1.7 mmol) was added, and the mixture was stirred for a further 2 h. Water (50 mL) was added, and the mixture was stirred for 10 min. The resulting mixture was then extracted with CH2Cl2 (200 mL). The CH2Cl2 layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 6-(chloromethyl)-2-(methylthio)benzo[d]thiazole (1.0 g, 88%) as a light red solid. The material was used in the next step without further purification. LCMS (ESI) m/z 230 (M+H)+.

1. customat −10° C.
2. stirringthe mixture was stirred for a further 2 h
3. stirringthe mixture was stirred for 10 min
4. extractionThe resulting mixture was then extracted with CH2Cl2 (200 mL)
5. customThe CH2Cl2 layer was separated
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-6d20588d37a847bf897ffea832a98157

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952058B2