Water → HCID 67983207, compound

HRID 2176424Notes

Reaction equation

HRID 2176424 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:14][C:15]#[N:16])[CH:7]=[C:8]([Cl:13])[C:9]=1[N:10]([CH3:12])[CH3:11].[F:17][C:18]([F:25])([F:24])[C:19](OCC)=[O:20].O>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:14]([C:19](=[O:20])[C:18]([F:25])([F:24])[F:17])[C:15]#[N:16])[CH:7]=[C:8]([Cl:13])[C:9]=1[N:10]([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydrideHCID 67982928HCID 67982928, compound

Product 1

HCID 67983207HCID 67983207, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1.41 g (35.3 mmol) of sodium hydride are initially charged in absolute THF (50 ml), and 4.05 g (17.6 mmol) of [3,5-dichloro-4-(dimethylamino)phenyl]acetonitrile in 20 ml of absolute THF are added dropwise at 0° C. The mixture is stirred at 0° C. for 20 minutes, and 5.02 g (35.3 mmol) of ethyl trifluoroacetate are then added dropwise at 0° C. The reaction mixture is warmed to room temperature and then carefully added to water. After washing with n-hexane, the aqueous phase is acidified with 1 N HCl. A colourless solid precipitates out and is, after filtration with suction and air-drying, used without further purification for the next step.

Workup

  1. temperatureThe reaction mixture is warmed to room temperature
  2. washAfter washing with n-hexane
  3. customA colourless solid precipitates out and
  4. filtrationafter filtration with suction
  5. customair-drying
  6. customused without further purification for the next step

Sources & evidence

ORD record
ord-aa9139cae5ac4c1787cef21cf49b5990
Source dataset
uspto-grants-2015_06
Patent number
US09066945B2

Reaction notes

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