Thiazole → 5-Phenylthiazole

HRID 1625847Notes

Reaction equation

HRID 1625847 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.I[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])(=O)C.[K+]>CN(C)C(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:7]1([C:5]2[S:1][CH:2]=[N:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 9256ThiazoleHCID 11575IodobenzeneHCID 517044Potassium Acetate

Product 1

HCID 5952095-Phenylthiazole

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of thiazole (10.0 g), iodobenzene (2.63 ml), tetrakis(triphenylphosphine)palladium (0) (1.36 g) and potassium acetate (3.46 g) in N,N-dimethylacetamide (100 ml) was stirred under heating at 100° C. overnight. The solvent was evaporated under reduced pressure, and added to the residue was ethyl acetate. The mixture was washed successively with water and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-90:10) to give 5-phenylthiazole (1.50 g) as a pale yellow solid. APCI-Mass m/Z 162 (M+H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionadded to the residue
  3. washThe mixture was washed successively with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-90:10)

Sources & evidence

ORD record
ord-f87d05c106264f5b80bd27c31c67211e
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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