Ethyl Acetoacetate → HCID 24810557, compound

HRID 1919576Notes

Reaction equation

HRID 1919576 reaction equation
C(O)(=O)C.[C:5]([NH:8][C:9]1[S:10][C:11]([C:14]([NH2:16])=[NH:15])=[CH:12][N:13]=1)(=[O:7])[CH3:6].[Cl:17][C:18]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:19]=1[CH:20]=O.[C:27]([O:33][CH2:34][CH3:35])(=[O:32])[CH2:28][C:29]([CH3:31])=O.C([O-])(=O)C.[Na+]>C(O)C>[C:5]([NH:8][C:9]1[S:10][C:11]([C:14]2[NH:16][C:29]([CH3:31])=[C:28]([C:27]([O:33][CH2:34][CH3:35])=[O:32])[CH:20]([C:19]3[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:18]=3[Cl:17])[N:15]=2)=[CH:12][N:13]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 136381431HCID 136381431, compound

Product 1

HCID 24810557HCID 24810557, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol 2-Acetylaminothiazol-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 0.32 g of a yellowish solid with mp>250° C.; 1H-NMR (400 MHz, DMSO-d6) δ 1.0-1.05 (3H, m); 2.14 (3H, s); 2.43 (3H, s); 2.59 (3H, s); 3.89-3.94 (2H, m); 5.89 (1H, s); 7.14-7.39 (3H, m); 8.11 (1H, s); 9.43 (1H, s); 12.22 (1H, br); MS (EI) 436.0 (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-70132009236e4596bdcbfb635c9c183f
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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