2-Chloro-1,1,1-triethoxyethane → 2-(Chloromethyl)-[1,3]thiazolo[5,4-b]pyridine

HRID 1768368Notes

Reaction equation

HRID 1768368 reaction equation
[NH2:1][C:2]1[C:3]([SH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:9][CH2:10][C:11](OCC)(OCC)OCC>C(O)C>[Cl:9][CH2:10][C:11]1[S:8][C:3]2[C:2]([N:1]=1)=[CH:7][CH:6]=[CH:5][N:4]=2

Participants

4

Reactant 2

HCID 3059222-Chloro-1,1,1-triethoxyethaneHCID 178418545HCID 178418545, compound

Product 1

HCID 142042072-(Chloromethyl)-[1,3]thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Amino-2-pyridinethiol (5.0 g, 39.6 mmol) and 2-chloro-1,1,1-triethoxyethane (8.57 g, 43.5 mmol) were combined in absolute ethanol (40 mL) and refluxed for 2 hours. The mixture was concentrated under reduced pressure and the residue purified by flash chromatography (ethyl acetate:hexanes, 1:4) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 4.93 (s, 2H) 7.47 (dd, J=8.14, 4.75 Hz, 1H) 8.26 (dd, J=8.31, 1.53 Hz, 1H) 8.62 (dd, J=4.58, 1.53 Hz, 1H). (ESI) m/z 186 (M+H)+.

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue purified by flash chromatography (ethyl acetate:hexanes, 1:4)

Sources & evidence

ORD record
ord-89463eb54c2d42fa8812027c0011c9fe
Source dataset
uspto-grants-2007_06
Patent number
US07235661B2

Reaction notes

Loading…