Sodium hydride → HCID 11224875, compound

HRID 1726844Notes

Reaction equation

HRID 1726844 reaction equation
[C:1]([C:3]([NH:7][C:8](=[O:20])[C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)([CH3:6])[CH2:4][OH:5])#[N:2].F[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[C:30]([F:33])([F:32])[F:31])[C:25]#[N:26].[H-].[Na+]>O1CCCC1>[C:1]([C:3]([NH:7][C:8](=[O:20])[C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)([CH3:6])[CH2:4][O:5][C:22]1[CH:23]=[C:24]([C:25]#[N:26])[CH:27]=[CH:28][C:29]=1[C:30]([F:31])([F:33])[F:32])#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27375503-Fluoro-4-(trifluoromethyl)benzonitrileHCID 67246452HCID 67246452, compound

Product 1

HCID 11224875HCID 11224875, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml of dried tetrahydrofurane, 651 mg N-[1-cyano-2-hydroxy-1-methylethyl]-4-trifluoromethoxybenzamide and 427 mg 3-fluoro-4-trifluoromethylbenzonitrile are dissolved and 63 mg of sodium hydride are added under stirring at 0°. The reaction mixture is stirred for 20 h at room temperature, then quenched with 5 ml of water and finally diluted with 15 ml of brine. The crude product is extracted with 3×10 ml of ethylacetate, the combined organic phases washed with brine, dried over magnesium sulphate, filtered and evaporated. The residue is purified by flash chromatography to yield the title compound as white crystals of m. p. 75-8°.

Workup

  1. stirringThe reaction mixture is stirred for 20 h at room temperature
  2. customquenched with 5 ml of water
  3. additionfinally diluted with 15 ml of brine
  4. extractionThe crude product is extracted with 3×10 ml of ethylacetate
  5. washthe combined organic phases washed with brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-b0a14d9fadf24d88a358b9f13bd03afb
Source dataset
uspto-grants-2009_02
Patent number
US07494956B2

Reaction notes

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