Potassium Carbonate → HCID 68537906, compound

HRID 1931450Notes

Reaction equation

HRID 1931450 reaction equation
[C:1]1([C:7]2[S:11][C:10]([NH2:12])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C=O)C>[C:24]([O:23][C:21](=[O:22])[CH2:20][NH:12][C:10]1[S:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][N:9]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 2194082-Amino-5-phenyl-1,3,4-thiadiazole

Product 1

HCID 68537906HCID 68537906, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g (5.6 mmol) of 5-phenyl-[1,3,4]thiadiazol-2-ylamine was dissolved in 20 ml of DMF, and 3.1 g (22.6 mmol) of potassium carbonate and 1.1 g (5.6 mmol) of tert-butyl bromoacetate were added. The reaction mixture was stirred at room temperature for 16 h. After evaporation of the solvent under reduced pressure, ethyl acetate was added to the residue. The solution was washed with water, dried with sodium sulfate, filtered, and the solvent was removed under reduced pressure. The product was purified by silica gel chromatography. Yield: 300 mg.

Workup

  1. customAfter evaporation of the solvent under reduced pressure, ethyl acetate
  2. additionwas added to the residue
  3. washThe solution was washed with water
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-562b957c83004b65b0eda55b7944b420
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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