Ethyl Acetate → HCID 18393045, compound

HRID 1739505Notes

Reaction equation

HRID 1739505 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[N:7][N:6]=1)[CH3:4].[I:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:3]([C:5]1[S:9][C:8](=[N:10][C:11](=[O:16])[C:12]([F:14])([F:15])[F:13])[N:7]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([I:17])=[CH:19][CH:20]=2)[N:6]=1)[CH3:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 9542584-Iodobenzyl bromideHCID 1221966HCID 1221966, compound

Product 1

HCID 18393045HCID 18393045, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (0.44 g) in N,N-dimethylformamide (10 ml) was added 5-ethyl-2-trifluoroacetylamino-1,3,4-thiadiazole (2.25 g) in three portions on ice. After the resulting mixture was stirred at the same temperature for 30 minutes, to the mixture was added 4-iodobenzyl bromide (2.97 g), and the mixture was stirred at room temperature for two hours. To the reaction mixture, ethyl acetate (50 ml) was added. The resulting mixture was washed successively with 10% aqueous citric acid solution and water and dried over anhydrous magnesium sulfate, followed by the removal through distillation. The residue so obtained was crystallized from n-hexane, collected by filtration and then dried, whereby 2.2 g of the title compound was obtained.

Workup

  1. stirringthe mixture was stirred at room temperature for two hours
  2. washThe resulting mixture was washed successively with 10% aqueous citric acid solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customfollowed by the removal through distillation
  5. customThe residue so obtained
  6. customwas crystallized from n-hexane
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-000259fed9af4133a9bee68b2fe5faf6
Source dataset
uspto-grants-1999_10
Patent number
US05965738

Reaction notes

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