Water → HCID 66794299, compound

HRID 1038324Notes

Reaction equation

HRID 1038324 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[N:16]([CH:17]=2)[C:15]2[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=2[S:13]3)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][Cl:32].O>CN(C=O)C>[Cl:32][CH2:31][CH2:30][O:22][C:20]1[CH:19]=[CH:18][C:15]2[N:16]3[CH:17]=[C:10]([C:7]4[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=4)[N:11]=[C:12]3[S:13][C:14]=2[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 299332572-(4-Nitrophenyl)imidazo[2,1-b]benzothiazol-7-ol

Product 1

HCID 66794299HCID 66794299, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(4-nitrophenyl)imidazo[2,2-b]benzothiazol-7-ol (2) (1 equivalent) in anhydrous DMF at rt are added potassium carbonate (2-3 equivalents) and 1-bromo-2-chloroethane (2-3 equivalents), and the mixture is stirred at a temperature between rt and 60° C. until the reaction is substantially complete as monitored by LCMS or TLC. The mixture is added to water and the resulting aqueous mixture is extracted with EtOAc. The organic layer is separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel flash chromatography to afford 7-(2-chloro-ethoxy)-2-(4-nitro-phenyl)-benzo[d]imidazo[2,1-b]thiazole.

Workup

  1. extractionthe resulting aqueous mixture is extracted with EtOAc
  2. customThe organic layer is separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-5bde52277aa343a98931214b17ee8610
Source dataset
uspto-grants-2013_10
Patent number
US08551963B2

Reaction notes

Loading…