Sodium hydride → HCID 11144181, compound

HRID 1416405Notes

Reaction equation

HRID 1416405 reaction equation
[H-].[Na+].[F:3][C:4]([F:16])([F:15])[C:5]([NH:7][C:8]1[S:9][C:10]([CH2:13][CH3:14])=[N:11][N:12]=1)=[O:6].[H][H].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]#[N:34])=[CH:23][CH:22]=1>CN(C)C=O>[F:16][C:4]([F:15])([F:3])[C:5]([N:7]=[C:8]1[N:12]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]#[N:34])=[CH:25][CH:26]=2)[N:11]=[C:10]([CH2:13][CH3:14])[S:9]1)=[O:6]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 1221966HCID 1221966, compoundHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 178418361HCID 178418361, compound

Product 1

HCID 11144181HCID 11144181, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 124.1 g of sodium hydride (55% dispersion in oil) in 1.5 liters of N,N-dimethylformamide was added 533.7 g of 2-trifluoroacetamido-5-ethyl-1,3,4-thiadiazole on ice. After the evolution of hydrogen subsided, a solution of 643.6 g of 4'-bromomethyl-2-cyanobiphenyl in 3 liters of N,N-dimethylformamide was added dropwise. The resulting mixture was stirred at room temperature for one hour and then at 80° C. for 5 hours, followed by concentration under reduced pressure. Water and ethyl acetate were added to the concentrate. The organic layer was then washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a 3:1 mixture of hexane and ethyl acetate. Crude crystals were recrystallized from ethanol, whereby 490.8 g of the title compound was obtained.

Workup

  1. waitat 80° C. for 5 hours
  2. concentrationfollowed by concentration under reduced pressure
  3. additionWater and ethyl acetate were added to the concentrate
  4. washThe organic layer was then washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with a 3:1 mixture of hexane and ethyl acetate
  8. customCrude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-8793fd0951364512b8c0372834fb8d46
Source dataset
uspto-grants-1999_06
Patent number
US05912353

Reaction notes

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