Ethyl Acetoacetate → HCID 24810555, compound

HRID 1919579Notes

Reaction equation

HRID 1919579 reaction equation
Cl.[Cl:2][C:3]1[S:4][C:5]([C:8]([NH2:10])=[NH:9])=[CH:6][N:7]=1.[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:4][C:5]([C:8]2[NH:10][C:23]([CH3:25])=[C:22]([C:21]([O:27][CH2:28][CH3:29])=[O:26])[CH:14]([C:13]3[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:12]=3[Cl:11])[N:9]=2)=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 67499792HCID 67499792, compound

Product 1

HCID 24810555HCID 24810555, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol 2-chlorothiazol-5-formamidine 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 yellow crystal with mp 159-162° C.; 1H-NMR (400 MHz, DMSO-d6) δ 1.0-1.03 (3H, m); 2.43 (3H, s); 3.92-3.95 (2H, m); 5.91 (1H, s); 7.16-7.41 (3H, m); 8.31 (1H, s); 9.69 (1H, s); MS (EI) 413.0 (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-eb9b2811bcbc46cbafd19abe4709b53c
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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