Ethyl Acetate → HCID 18393045, compound

HRID 1739506Notes

Reaction equation

HRID 1739506 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[N:5][N:4]=1)[CH3:2].[I:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.CCCCCC>[CH2:1]([C:3]1[S:7][C:6](=[N:8][C:9](=[O:14])[C:10]([F:12])([F:13])[F:11])[N:5]([CH2:20][C:19]2[CH:22]=[CH:23][C:16]([I:15])=[CH:17][CH:18]=2)[N:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 9542584-Iodobenzyl bromideHCID 1221966HCID 1221966, compound

Product 1

HCID 18393045HCID 18393045, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a solution of 5-ethyl-2-trifluoroacetylamino-1,3,4-thiadiazole (22.5 g) and 4-iodobenzyl bromide (32.7 g) in N,N-dimethylformamide (100 ml) was added potassium carbonate (13.8 g), followed by stirring at room temperature overnight. To the reaction mixture, ethyl acetate (500 ml) was added. The resulting mixture was washed three times with 10% aqueous citric acid solution, followed by drying over anhydrous magnesium sulfate. The solvent was then distilled off. The oily substance so obtained was separated by column chromatography on silica gel. The crystals so obtained were dispersed in n-hexane, collected by filtration and then dried, whereby 33.9 g of the title compound was obtained.

Workup

  1. washThe resulting mixture was washed three times with 10% aqueous citric acid solution
  2. dry with materialby drying over anhydrous magnesium sulfate
  3. distillationThe solvent was then distilled off
  4. customThe oily substance so obtained
  5. customwas separated by column chromatography on silica gel
  6. customThe crystals so obtained
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-b5c2e6d6d2d448569fd4fe0f04ba8076
Source dataset
uspto-grants-1999_10
Patent number
US05965738

Reaction notes

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