Aluminium lithium hydride → HCID 21914903, compound

HRID 2117952Notes

Reaction equation

HRID 2117952 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:17]=2)=[C:8]([C:10](OCC)=[O:11])[N:9]=1)(=[O:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:10]([C:8]1[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:17]=1)=[O:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21915026HCID 21915026, compound

Product 1

HCID 21914903HCID 21914903, compoundYield 126.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(acetylamino)-5-[3-(methylsulfonyl)benzyl]-1,3-thiazole-4-carboxylate (54.7 mg) was suspended in THF (1 ml) under N2 atmosphere, and then lithium aluminium hydride (7.79 mg) was added portionwise to the suspension at 0° C. The reaction mixture was refluxed for 2.5 hours, and quenched with MeOH and 1N—HCl at 0° C. Anhydrous MgSO4 was added to the mixture, and stirred at r.t. for 1 hour. The suspension was filtered in vacuo. The filtrate was concentrated in vacuo. The residual oil (114.8 mg), CHCl3 (1 ml), CH3CN (1 ml) and Dess-Martin periodinane (88 mg) were combined at 0° C. under N2 atmosphere. The reaction mixture was stirred at r.t. for 1 hour, and diluted in CHCl3. The organic solution was washed with saturated NaHCO3, water and brine, dried over anhydrous MgSO4, and concentrated in vacuo to give N-{4-formyl-5-[3-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide (61.2 mg) as a yellow amorphous.

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 hours
  2. customquenched with MeOH and 1N—HCl at 0° C
  3. additionAnhydrous MgSO4 was added to the mixture
  4. filtrationThe suspension was filtered in vacuo
  5. concentrationThe filtrate was concentrated in vacuo
  6. customwere combined at 0° C. under N2 atmosphere
  7. stirringThe reaction mixture was stirred at r.t. for 1 hour
  8. additiondiluted in CHCl3
  9. washThe organic solution was washed with saturated NaHCO3, water and brine
  10. dry with materialdried over anhydrous MgSO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ded2520e24045f299a9458bbd9e9d84
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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