Methyl acetoacetate → HCID 59272686, compound

HRID 1919571Notes

Reaction equation

HRID 1919571 reaction equation
C(O)(=O)C.[CH3:5][C:6]1[N:7]=[CH:8][S:9][C:10]=1[C:11]([NH2:13])=[NH:12].[Cl:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=1[CH:17]=O.[C:24]([O:30][CH3:31])(=[O:29])[CH2:25][C:26]([CH3:28])=O.C([O-])(=O)C.[Na+]>C(O)C>[CH3:5][C:6]1[N:7]=[CH:8][S:9][C:10]=1[C:11]1[NH:13][C:26]([CH3:28])=[C:25]([C:24]([O:30][CH3:31])=[O:29])[CH:17]([C:16]2[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:15]=2[Cl:14])[N:12]=1

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 67500107HCID 67500107, compound

Product 1

HCID 59272686HCID 59272686, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol 4-methyl-5-thiazolformamidine acetate, 2 mmol 2-chloro-4-fluorobenzaldehyde, 2 mmol methyl 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 0.24 g of a colorless crystal with mp 145-147° C.; 1H-NMR (400 MHz, DMSO-d6) δ 2.34 (3H, s); 2.38 (3H, s); 3.50 (3H, s); 5.95 (1H, s); 7.12-7.49 (3H, m); 9.08 (1H, s); 9.61 (1H, s); MS (EI) 379.0 (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-86967fb6dba84520ae0926421b35db35
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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