Diethyl Malonate → 2-(2,2,2-Trifluoro-1-phenylimino-ethyl)-malonic acid diethyl ester

HRID 2189514Notes

Reaction equation

HRID 2189514 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[F:14][C:15]([F:26])([F:25])[C:16](Cl)=[N:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.C(Cl)Cl>[CH2:12]([O:11][C:3](=[O:10])[CH:4]([C:16](=[N:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15]([F:14])([F:25])[F:26])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]

Participants

6

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 100588692,2,2-Trifluoro-N-phenylacetimidoyl Chloride

Product 1

HCID 572200902-(2,2,2-Trifluoro-1-phenylimino-ethyl)-malonic acid diethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (3.47 g, 145 mmol, 60% in mineral oil) in THF (200 mL) was added diethyl malonate (18.5 g, 116 mmol) at 0° C. The mixture was stirred for 30 min at this temperature and 2,2,2-trifluoro-N-phenyl-acetimidoyl chloride (19 g, 92 mmol) was added at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was diluted with CH2Cl2, washed with saturated sodium bicarbonate solution and brine. The combined organic layers were dried over Na2SO4, filtered and concentrated to provide 2-(2,2,2-trifluoro-1-phenylimino-ethyl)-malonic acid diethyl ester, which was used directly in the next step without further purification.

Workup

  1. additionwas added at 0° C
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f5c9a25d64044025836daf34762ef65a
Source dataset
uspto-grants-2012_12
Patent number
US08324242B2

Reaction notes

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