Ethyl Acetoacetate → HCID 23726010, compound

HRID 1919581Notes

Reaction equation

HRID 1919581 reaction equation
CS(O)(=O)=O.[CH3:6][NH:7][C:8]([C:10]1[NH:11][CH:12]=[CH:13][N:14]=1)=[NH:9].[Cl:15][C:16]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:17]=1C=O.[C:25]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:26][C:27]([CH3:29])=O.[C:34]([O-])(=O)C.[Na+]>C(O)C>[CH3:34][N:11]1[CH:12]=[CH:13][N:14]=[C:10]1[C:8]1[NH:9][C:27]([CH3:29])=[C:26]([C:25]([O:31][CH2:32][CH3:33])=[O:30])[CH:6]([C:17]2[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:16]=2[Cl:15])[N:7]=1

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 178484930HCID 178484930, compound

Product 1

HCID 23726010HCID 23726010, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol N-methyl-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 0.23 g of a yellowish columnar crystal with mp 166-167° C.; 1H-NMR (400 MHz, DMSO-d6) δ 1.03-1.06 (3H, m); 2.48 (3H, s); 3.81 (1H, s); 3.93-3.99 (2H, m); 6.00 (1H, s); 6.99-7.42 (5H, m); 9.57 (1H, s); MS (EI) 376.1 (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 0.23 g of a yellowish columnar crystal with mp 166-167° C.

Sources & evidence

ORD record
ord-a347bde053a04ed88726f47a80d88a2e
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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