Ethyl Acetoacetate → HCID 24810559, compound

HRID 1919574Notes

Reaction equation

HRID 1919574 reaction equation
C(O)(=O)C.[CH3:5][C:6]1[S:7][C:8]([C:11]([NH2:13])=[NH:12])=[CH:9][N:10]=1.[Cl:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=1[CH:17]=O.[C:24]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:25][C:26]([CH3:28])=O.C([O-])(=O)C.[Na+]>C(O)C>[CH3:5][C:6]1[S:7][C:8]([C:11]2[NH:13][C:26]([CH3:28])=[C:25]([C:24]([O:30][CH2:31][CH3:32])=[O:29])[CH:17]([C:16]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:15]=3[Cl:14])[N:12]=2)=[CH:9][N:10]=1

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 67499486HCID 67499486, compound

Product 1

HCID 24810559HCID 24810559, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol 2-Methylthiazol-5-formamidine acetate, 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 0.24 g of a yellowish solid with mp 107-111° C.; 1H-NMR (400 MHz, DMSO-d6) δ 1.0-1.04 (3H, m); 2.43 (3H, s); 2.59 (3H, s); 3.89-3.93 (2H, m); 5.90 (1H, s); 7.14-7.43 (3H, m); 9.52 (1H, s); MS (EI) 393.0 (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

Sources & evidence

ORD record
ord-b95dab03228b4b75ab0f59287b5dc47f
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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