Acrylamide → 3-[{2-(1,3-Benzodioxol-5-yl)ethyl}thio]propionamide

HRID 2259742Notes

Reaction equation

HRID 2259742 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][SH:12])=[CH:9][C:4]=2[O:3][CH2:2]1.[C:13]([NH2:17])(=[O:16])[CH:14]=[CH2:15]>C(O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][S:12][CH2:15][CH2:14][C:13]([NH2:17])=[O:16])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 6579AcrylamideHCID 158195122-(1,3-Benzodioxol-5-yl)ethanethiol

Product 1

HCID 190016823-[{2-(1,3-Benzodioxol-5-yl)ethyl}thio]propionamideYield 60.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5 g of 2-(1,3-benzodioxol-5-yl)ethanethiol and 4 g of acrylamide were dissolved in 100 ml of ethanol and the solution was heated under reflux to conduct the reaction for 20 h. The reaction mixture was cooled with ice. 100 ml of ethanol was added thereto and crystals thus formed were recovered by filtration to obtain 4.2 g of the intended compound in the form of colorless needles.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux
  3. customthe reaction for 20 h
  4. temperatureThe reaction mixture was cooled with ice
  5. customcrystals thus formed
  6. filtrationwere recovered by filtration

Sources & evidence

ORD record
ord-47aaf99627ea4e2093946d2b4eb65c62
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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