Hydrochloric Acid → 2-(1H-Imidazol-2-yl)-1,3-thiazole

HRID 1594065Notes

Reaction equation

HRID 1594065 reaction equation
Cl.C(OC[N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11]1[S:12][CH:13]=[CH:14][N:15]=1)C.[OH-].[Na+].C([O-])(O)=O.[Na+]>C(O)C.O>[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:11]1[S:12][CH:13]=[CH:14][N:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 222603972-(1-ethoxymethyl-1H-imidazol-2-yl)-thiazole

Product 1

HCID 222603952-(1H-Imidazol-2-yl)-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
0 °C

Procedure

Concentrated HCl (10 ml) is added to a solution of 2-(1-ethoxymethyl-1H-imidazol-2-yl)-thiazole (940 mg, 4.49 mmol) in 24 mL of 1:1 EtOH-H2O at room temperature. The solution is stirred at reflux for 3 h. The reaction mixture is then cooled to 0° C. and made basic by the addition of about 12 mL of 10 N aqueous NaOH. The mixture is back titrated to approximately pH 4 using concentrated HCl. Solid NaHCO3 is added to the point of saturation and approximately pH 8. The mixture is then extracted twice using a mixture of THF and EtOAc. The combined extracts are dried over Na2SO4 and concentrated to an oily solid, which is triturated with a small amount of CH2Cl2. The solid is collected by filtration. The filtrate is concentrated, and the oily solid triturated once more with CH2Cl2. The second resultant solid is collected by filtration and combined with the solid first obtained. The product, 2-(1H-imidazol-2-yl)-thiazole, is obtained as a slightly off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.04 (br, 1H), 7.87 (d, J=3.2 Hz, 1H), 7.70 (d, J=3.2 Hz, 1H) 7.14 (br, 2H) ppm.

Workup

  1. temperatureat reflux for 3 h
  2. extractionThe mixture is then extracted twice
  3. additiona mixture of THF and EtOAc
  4. dry with materialThe combined extracts are dried over Na2SO4
  5. concentrationconcentrated to an oily solid, which
  6. customis triturated with a small amount of CH2Cl2
  7. filtrationThe solid is collected by filtration
  8. concentrationThe filtrate is concentrated
  9. customthe oily solid triturated once more with CH2Cl2
  10. filtrationThe second resultant solid is collected by filtration

Sources & evidence

ORD record
ord-7914d6a2144b488293008b45e9e36cf4
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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