Water → HCID 19421602, compound

HRID 1613308Notes

Reaction equation

HRID 1613308 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:10][C:11]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=O)=[CH:5][CH:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1.O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:10][C:11]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[S:36])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 19421679HCID 19421679, compound

Product 1

HCID 19421602HCID 19421602, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.155 g of the 1-[3,3-bis(4-methoxyphenyl)acryloyl]piperazine [prepared as described in step (a) above] were dissolved in 12 ml of benzene, and the resulting solution was heated under reflux for 2 hours with 1.326 g of Lawesson's Reagent. At the end of this time, the reaction mixture was cooled to room temperature, after which it was poured into water and extracted twice with ethyl acetate. The combined extracts were washed with water, dried over anhydrous sodium sulfate, and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through 30 g of silica gel eluted with a 19:1 by volume mixture of methylene chloride and methanol, to give 1.177 g of 1-[3,3-bis(4-methoxyphenyl)thioacryloyl]piperazine as a powder.

Workup

  1. temperaturethe resulting solution was heated
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue was purified by column chromatography through 30 g of silica gel
  7. washeluted with a 19:1 by volume mixture of methylene chloride and methanol

Sources & evidence

ORD record
ord-b059d936d5af4349b2b200f0e5483b9a
Source dataset
uspto-grants-1993_03
Patent number
US05192766

Reaction notes

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