Ethyl Acetoacetate → HCID 24810501, compound

HRID 1919582Notes

Reaction equation

HRID 1919582 reaction equation
CS(O)(=O)=O.[CH2:6]([NH:13][C:14]([C:16]1[NH:17][CH:18]=[CH:19][N:20]=1)=[NH:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:21][C:22]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:23]=1[CH:24]=O.[C:31]([O:37][CH2:38][CH3:39])(=[O:36])[CH2:32]C(C)=O.[C:40]([O-])(=O)[CH3:41].[Na+]>C(O)C>[CH2:6]([N:13]1[CH:41]=[CH:40][N:15]=[C:14]1[C:16]1[NH:20][C:19]([CH3:18])=[C:32]([C:31]([O:37][CH2:38][CH3:39])=[O:36])[CH:24]([C:23]2[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:22]=2[Cl:21])[N:17]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 178505348HCID 178505348, compound

Product 1

HCID 24810501HCID 24810501, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol N-benzyl-1H-imidazol-2-formamidine methane sulfonate (Tommasi, R. A., Macchia, W. M., Parker, D. T., Tetrahedron Lett 1998, 39:5947-5950), 2 mmol 2-chloro-4-fluorobenzaldehyde, 2 mmol ethyl acetoacetate and 2.2 mmol sodium acetate were reacted under reflux in 10 ml anhydrous ethanol for 20 hr, concentrated, and then ethyl acetate and water were added to separate the layers. The ethyl acetate layer was dried over anhydrous sodium sulfate, and separated by a column chromatography to obtain 0.31 g of colorless granulates with mp 114-117° C.; 1H-NMR (400 MHz, DMSO-d6) δ 1.0-1.05 (3H, m, J=7.0 Hz); 2.46 (3H, s); 3.91-3.96 (2H, m, J=7.0 Hz); 5.43-5.46 (1H, d, J=14.3 Hz); 5.81-5.85 (1H, d, J=14.3 Hz); 6.00 (1H, s); 6.92-7.5 (10H, m); 9.57 (1H, s); MS (EI) 452.1 (M+).

Workup

  1. concentrationconcentrated
  2. additionethyl acetate and water were added
  3. customto separate the layers
  4. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  5. customseparated by a column chromatography
  6. customto obtain 0.31 g of colorless granulates with mp 114-117° C.

Sources & evidence

ORD record
ord-272fdb211eae4b84a1a3f7097f29bfd2
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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