Sodium Iodide → 6-(3-Picolinyloxy)-2-cyanobenzothiazole

HRID 1618095Notes

Reaction equation

HRID 1618095 reaction equation
[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].Br.Br[CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CC(C)=O>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][O:12][C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:3]([C:1]#[N:2])[S:4][C:5]=3[CH:11]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 98819122-Cyano-6-hydroxybenzothiazoleHCID 127070373-(Bromomethyl)pyridine hydrobromide

Product 1

HCID 584277706-(3-Picolinyloxy)-2-cyanobenzothiazoleYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-cyano-6-hydroxybenzothiazole (0.39 g, 2.2 mmol) in acetone (50 mL) was added 3-(bromomethyl)pyridine hydrobromide (0.7 g, 2.76 mmol), cesium carbonate (2.15 g, 6.6 mmol), and a catalytic amount of sodium iodide. After adding 3A molecular sieves, the yellow suspension was refluxed for 40 h under nitrogen. After cooling down the mixture and filtering the solids, the filtrate was concentrated and the residue was purified by silica gel chromatography using 50%-100% ethyl acetate in heptane. A yellowish solid was obtained in 61% yield. MS (ESI+): m/z 267.64 (M+H)+; calc'd: 268.05.

Workup

  1. temperaturethe yellow suspension was refluxed for 40 h under nitrogen
  2. temperatureAfter cooling down the mixture
  3. filtrationfiltering the solids
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified by silica gel chromatography
  6. customA yellowish solid was obtained in 61% yield

Sources & evidence

ORD record
ord-0bf7f6477d1f4d6faa17614b9547f876
Source dataset
uspto-grants-2014_07
Patent number
US08765969B2

Reaction notes

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