Thioacetamide → HCID 66673711, compound

HRID 421835Notes

Reaction equation

HRID 421835 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].Br[CH2:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)=O>C(O)C>[CH3:2][C:1]1[S:3][CH:6]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[N:4]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 15829155tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylate

Product 1

HCID 66673711HCID 66673711, compoundYield 2.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thioacetamide (120 mg) was added to an ethanol (6 mL) solution of tert-butyl 4-(bromoacetyl)piperazinecarboxylate (340 mg) obtained in the above 1), and heated under reflux for 3 hours. The reaction liquid was restored to room temperature, then the solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=7/3) to obtain 7 mg of the entitled compound.

Workup

  1. customobtained in the above 1), and
  2. temperatureheated
  3. temperatureunder reflux for 3 hours
  4. customThe reaction liquid
  5. customwas restored to room temperature
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-5049bb1cc5e24c538645131813f4771e
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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