Ethyl Acetoacetate → HCID 59272678, compound

HRID 1919557Notes

Reaction equation

HRID 1919557 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([NH2:8])=[NH:7])[N:3]=[CH:2]1.[Cl:9][C:10]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:11]=1[CH:12]=O.[C:19]([O:25][CH2:26][CH3:27])(=[O:24])[CH2:20][C:21]([CH3:23])=O.C([O-])(=O)C.[Na+]>C(O)C>[S:1]1[CH:5]=[C:4]([C:6]2[NH:8][C:21]([CH3:23])=[C:20]([C:19]([O:25][CH2:26][CH3:27])=[O:24])[CH:12]([C:11]3[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:10]=3[Cl:9])[N:7]=2)[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 55281003HCID 55281003, compound

Product 1

HCID 59272678HCID 59272678, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol 4-Thiazolyl formamidine (Diana, G. D., Yarinsky, A., Zalay, E. S., et al. J. Med. Chem. 1969, 12(9):791-793), 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 0.28 g of a yellow crystal (yield 37%) with mp 140-142° C.; 1H-NMR (400 MHz, DMSO-d6) δ 1.01-1.05 (3H, m); 2.49 (3H, s); 3.92-3.95 (2H, m); 5.99 (1H, s); 7.36-7.39 (3H, m); 8.15 (1H, d, J=1.96 Hz); 9.18 (1H, d, J=1.96 Hz); 9.47 (1H, s); MS (FAB) 380.2 (M+1).

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-11cbb9103d494f50a02fc749002ca473
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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