Ethyl Acetoacetate → HCID 59272711, compound

HRID 1919569Notes

Reaction equation

HRID 1919569 reaction equation
Cl.[Cl:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([NH2:10])=[NH:9])[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][CH:5]=[C:6]([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)[N:7]=1

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 66769369HCID 66769369, compound

Product 1

HCID 59272711HCID 59272711, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol 2-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 0.28 g of a yellowish crystal with mp 141-143° C.; 1H-NMR (400 MHz, DMSO-d6) δ 1.01-1.05 (3H, m); 2.42 (3H, s); 3.92-3.95 (2H, m); 5.97 (1H, br); 7.16-7.40 (3H, m); 8.09 (1H, s); 9.52 (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-c8a34c6603f04c8c9f28450051e36866
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

Loading…