Potassium Carbonate → 2-(5-Amino-3-methylsulfanyl-[1,2,4]triazol-1-yl)-1-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethanone

HRID 270918Notes

Reaction equation

HRID 270918 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[C:5]([NH2:8])[NH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18]>CN(C=O)C>[NH2:8][C:5]1[N:6]([CH2:16][C:17]([N:19]2[CH2:20][CH2:21][N:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[CH2:23][CH2:24]2)=[O:18])[N:7]=[C:3]([S:2][CH3:1])[N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 784713-(Methylthio)-1,2,4-triazol-5-amineHCID 40539571-(Chloroacetyl)-4-(4-chlorophenyl)piperazine

Product 1

HCID 210711172-(5-Amino-3-methylsulfanyl-[1,2,4]triazol-1-yl)-1-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-Methylsulfanyl-2H-[1,2,4]triazol-3-ylamine (0.216 g, 1.7 mmol) was taken in dry DMF (15 ml) and dry potassium carbonate (800 mg) and KI (20 mg) was added to it and the reaction mixture stirred at room temperature for 1 h under nitrogen. 2-Chloro-1-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethanone (500 mg, 1.8 mmol) in DMF (5 ml) was then added to the mixture through a syringe. The reaction was then heated at 140° C. for 14 h, cooled and then quenched with water and extracted with ethyl acetate. Drying of the organic layer with Na2SO4 followed by concentration afforded crude product that was purified by column chromatography (CHCl3/MeOH): 1H NMR (300 MHz, DMSO-d6): δ 7.24 (d, 2H), 6.98 (d, 2H), 6.24 (s, 2H), 4.84 (s, 2H), 3.57 (m, 4H), 3.21 (m, 2H), 3.13 (m, 2H), 2.37 (s, 3H).

Workup

  1. temperatureThe reaction was then heated at 140° C. for 14 h
  2. temperaturecooled
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialDrying of the organic layer with Na2SO4
  6. concentrationfollowed by concentration
  7. customafforded crude product that
  8. customwas purified by column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-1ae4a254a63742c49fd58ca50df86da7
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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