Potassium Carbonate → 6-(2-Picolinyloxy)-2-cyanobenzothiazole

HRID 1618094Notes

Reaction equation

HRID 1618094 reaction equation
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[C:10]([C:12]1[S:13][C:14]2[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:15]=2[N:16]=1)#[N:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][O:21][C:19]1[CH:18]=[CH:17][C:15]2[N:16]=[C:12]([C:10]#[N:11])[S:13][C:14]=2[CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 98819122-Cyano-6-hydroxybenzothiazole

Product 1

HCID 584277576-(2-Picolinyloxy)-2-cyanobenzothiazoleYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(Bromomethyl)pyridine hydrobromide (1.87 g, 7.38 mmol) and 2-cyano-6-hydroxybenzothiazole (1.00 g, 5.68 mmol) were suspended in acetone (50 mL). After introduction of potassium carbonate (1.96 g, 14.2 mmol), the suspension was refluxed for 72 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%-75% ethyl acetate in heptane. A yellowish solid was obtained in 72% yield. MS (ESI+): m/z 267.90 (M+H)+; calc'd: 268.05.

Workup

  1. temperatureAfter cooling down the mixture
  2. filtrationfiltering the solids
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by silica gel chromatography
  5. customA yellowish solid was obtained in 72% yield

Sources & evidence

ORD record
ord-a4d766758998443a986515618fa3c2d0
Source dataset
uspto-grants-2014_07
Patent number
US08765969B2

Reaction notes

Loading…