Aluminium lithium hydride → HCID 21914992, compound

HRID 2117892Notes

Reaction equation

HRID 2117892 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=2)=[C:8]([C:10](OC)=[O:11])[N:9]=1)(=[O:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:10]([C:8]1[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=1[C:14]1[CH:15]=[CH:16][C:17]([S:20][CH3:21])=[CH:18][CH:19]=1)=[O:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21914785HCID 21914785, compound

Product 1

HCID 21914992HCID 21914992, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-(acetylamino)-5-[4-(methylthio)phenyl]-1,3-thiazole-4-carboxylate (200 mg) was dissolved in tetrahydrofuran (2 ml), and then lithium aluminium hydride (35.3 mg) was added portionwise to the solution at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes and at room temperature for 30 minutes, and quenched with methanol. Ethyl acetate and 1N hydrochloric acid were added to the mixture, and extracted. The aqueous layer was extracted with ethyl acetate (twice). The combined organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residual solid was dissolved in methanol (0.4 ml) and chloroform (7 ml). Then manganase (IV) oxide (1.08 g) was added to the solution under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 13 hours, and filtered through a celite pad. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with chloroform/methanol (20:1) as an eluent to give N-{4-formyl-5-[4-(methylthio)phenyl]-1,3-thiazol-2-yl}acetamide (153.6 mg) as a pale brown amorphous substance.

Workup

  1. customquenched with methanol
  2. additionEthyl acetate and 1N hydrochloric acid were added to the mixture
  3. extractionextracted
  4. extractionThe aqueous layer was extracted with ethyl acetate (twice)
  5. washThe combined organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residual solid was dissolved in methanol (0.4 ml)
  9. additionThen manganase (IV) oxide (1.08 g) was added to the solution under nitrogen atmosphere
  10. stirringThe reaction mixture was stirred at room temperature for 13 hours
  11. filtrationfiltered through a celite pad
  12. concentrationThe filtrate was concentrated in vacuo
  13. customThe residue was purified by flash column chromatography over silica gel with chloroform/methanol (20:1) as an eluent

Sources & evidence

ORD record
ord-e43078fb928d42e4bef52c6daa179253
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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