Methyl acetoacetate → HCID 24810449, compound

HRID 1919583Notes

Reaction equation

HRID 1919583 reaction equation
Cl.[F:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:4]=1[C:5]([NH2:7])=[NH:6].[Cl:13][C:14]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:15]=1[CH:16]=O.[C:23]([O:29][CH3:30])(=[O:28])[CH2:24][C:25]([CH3:27])=O.C([O-])(=O)C.[Na+]>C(O)C>[F:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:4]=1[C:5]1[NH:7][C:25]([CH3:27])=[C:24]([C:23]([O:29][CH3:30])=[O:28])[CH:16]([C:15]2[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:14]=2[Cl:13])[N:6]=1

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 463184242,6-Difluorobenzamidine hydrochloride

Product 1

HCID 24810449HCID 24810449, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol 2,6-Difluorobenzamidine hydrochloride (Boere, R. J., Oakley, R. T., Read, R. V., J. Organometal. Chem. 1987, 331:161-167), 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 0.21 g of a colorless fine needle crystal with mp 126-128° C.; 1H-NMR (400 MHz, DMSO-d6) δ 2.87 (3H, s); 3.45 (3H, s); 5.92 (1H, s); 7.10-7.38 (6H, m); 9.87 (1H, s); MS (EI) 394.0 (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-f15f158254ff4aa88de3e32271820ef2
Source dataset
uspto-grants-2012_05
Patent number
US08168642B2

Reaction notes

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