Potassium Acetate → HCID 18449359, compound

HRID 1921188Notes

Reaction equation

HRID 1921188 reaction equation
[OH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[C:12]1[S:13][CH:14]=[C:15]([Br:17])[N:16]=1.CC([O-])=O.[K+]>N1C=CC=CC=1.[Cu].Cl[Cu]>[Br:17][C:15]1[N:16]=[C:12]([N:3]2[C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[NH:6][C:2]2=[O:1])[S:13][CH:14]=1

Participants

7

Reactant 3

HCID 517044Potassium AcetateHCID 27632972,4-Dibromo-1,3-thiazoleHCID 178517141HCID 178517141, compound

Product 1

HCID 18449359HCID 18449359, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 62652Cuprous chlorideCatalystHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-hydroxybenzimidazole (1.20 g, 8.95 mmol), 2,4-dibromothiazole (6.50 g, 26.8 mmol), copper powder (1.42 g, 22.4 mmol), CuCl (177 mg, 1.79 mmol), and KOAc (2.20 g, 22.4 mmol) in pyridine (10 mL) were heated at 60° C. for 2 h. The cooled mixture was partitioned between EtOAc (40 mL) and 10% aqueous citric acid (20 mL) and the organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 50:50, to give the title compound. MS: m/z=298 (M+1).

Workup

  1. customThe cooled mixture was partitioned between EtOAc (40 mL) and 10% aqueous citric acid (20 mL)
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-1036193810df4a0ca5171de11251f4b1
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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