Azobisisobutyronitrile → Butyl 3-(2-(2-oxo-1,3-dioxolan-4-yl)ethylthio)propanoate

HRID 1486227Notes

Reaction equation

HRID 1486227 reaction equation
[CH:1]([CH:3]1[CH2:7][O:6][C:5](=[O:8])[O:4]1)=[CH2:2].[CH2:9]([O:13][C:14](=[O:18])[CH2:15][CH2:16][SH:17])[CH2:10][CH2:11][CH3:12].N(C(C)(C)C#N)=NC(C)(C)C#N>>[O:8]=[C:5]1[O:4][CH:3]([CH2:1][CH2:2][S:17][CH2:16][CH2:15][C:14]([O:13][CH2:9][CH2:10][CH2:11][CH3:12])=[O:18])[CH2:7][O:6]1

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 85335Butyl 3-mercaptopropionateHCID 27350381,3-Dioxolan-2-one, 4-ethenyl-

Product 1

HCID 118389509Butyl 3-(2-(2-oxo-1,3-dioxolan-4-yl)ethylthio)propanoate

Conditions

Temperature
110 °C

Procedure

3.87 grams (33.9 mmol, MW: 114.10) 4-vinyl-1,3-dioxaolane-2-one, 5.0 grams (30.8 mol, MW: 162.25) butyl-3-mercaptopropionate and 0.505 grams (3.1 mmol, MW: 164.21) 2,2′-azobis(2-methylpropionitrile) (AIBN) were charged in a 25 milliliter thick sealed glass reactor. After addition, the reaction mixture was stirred for 22 hours at 110° C. The reaction was then stopped and cooled down to room temperature. The excess of unreacted 4-vinyl-1,3-dioxaolane-2-one was removed by air bath oven at 180° C. under vacuum for 1 hour. The final product was determined by IR, 13CNMR. Yield: 4.26 grams (50%). IR: (cm−1) 2960, 2933, 2873, 1803, 1731, 1456, 1390, 1351, 1246, 1169, 1065, 772. 13C NMR (CDCl3): 171.7, 154.7, 124.6, 113.4, 75.4, 69.2, 64.5, 35.0, 33.9, 30.5, 27.2, 19.1, 13.7.

Workup

  1. customthick sealed glass reactor
  2. additionAfter addition
  3. temperaturecooled down to room temperature
  4. customThe excess of unreacted 4-vinyl-1,3-dioxaolane-2-one was removed by air bath oven at 180° C. under vacuum for 1 hour

Sources & evidence

ORD record
ord-1f0ecbfcecb34a16a3d0654fc8db0d59
Source dataset
uspto-grants-2016_08
Patent number
US09422502B2

Reaction notes

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