Thionyl Chloride → 6-(Chloromethyl)-2-(methylthio)thiazolo[4,5-b]pyridine

HRID 1848105Notes

Reaction equation

HRID 1848105 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[C:6]([N:13]=1)=[N:7][CH:8]=[C:9]([CH2:11]O)[CH:10]=2.O=S(Cl)[Cl:16]>C(Cl)Cl>[Cl:16][CH2:11][C:9]1[CH:10]=[C:5]2[S:4][C:3]([S:2][CH3:1])=[N:13][C:6]2=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86681080(2-(Methylthio)thiazolo[4,5-b]pyridin-6-yl)methanol

Product 1

HCID 866810816-(Chloromethyl)-2-(methylthio)thiazolo[4,5-b]pyridineYield 107.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of (2-(methylthio)thiazolo[4,5-b]pyridin-6-yl)methanol (404 mg, 2 mmol) in anhydrous CH2Cl2 (20 mL) at rt was added SOCl2 (166 μL, 2.4 mmol). After 3 h, the mixture was concentrated under reduced pressure to afford 6-(chloromethyl)-2-(methylthio)thiazolo[4,5-b]pyridine (497 mg) as a white solid. The material was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 8.65 (d, J=1.9 Hz, 1H), 8.60 (d, J=1.9 Hz, 1H), 4.95 (s, 2H), 2.83 (s, 3H); LCMS (ESI) m/z 231 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-969dde3d30044c2c87cb51d7d214e2a9
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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