Ethyl Acetoacetate → HCID 59272702, compound

HRID 1919567Notes

Reaction equation

HRID 1919567 reaction equation
Cl.[Cl:2][C:3]1[S:7][CH:6]=[N:5][C:4]=1[C:8]([NH2:10])=[NH:9].[Cl:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH:14]=O.[C:21]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:22][C:23]([CH3:25])=O.C([O-])(=O)C.[Na+]>C(O)C>[Cl:2][C:3]1[S:7][CH:6]=[N:5][C:4]=1[C:8]1[NH:10][C:23]([CH3:25])=[C:22]([C:21]([O:27][CH2:28][CH3:29])=[O:26])[CH:14]([C:13]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:12]=2[Cl:11])[N:9]=1

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 66769348HCID 66769348, compound

Product 1

HCID 59272702HCID 59272702, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol 5-chloro-4-thiazolformamidine hydrochloride, 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 0.29 g of a yellowish solid with mp 149-152° C.; 1H-NMR (400 MHz, DMSO-d6) δ 1.02-1.06 (3H, m); 2.42 (3H, s); 3.92-3.97 (2H, m); 6.01 (1H, br); 7.16-7.41 (3H, m); 9.08 (1H, s); 9.58 (1H, s); MS (EI) 413.1 (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

Sources & evidence

ORD record
ord-42a2bba0173f4fb285c8d6cbca455734
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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