Triethylamine → 4-(5-Ethylpyridin-2-yl)-1,3,2lambda~4~-dioxathiolan-2-one

HRID 2094812Notes

Reaction equation

HRID 2094812 reaction equation
C(N(CC)CC)C.[CH2:8]([C:10]1[CH:11]=[CH:12][C:13]([CH:16]([OH:19])[CH2:17][OH:18])=[N:14][CH:15]=1)[CH3:9].[S:20](Cl)(Cl)=[O:21]>ClCCl>[CH2:8]([C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[CH2:17][O:18][S:20](=[O:21])[O:19]2)=[N:14][CH:15]=1)[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 232222451-(5-Ethylpyridin-2-yl)ethane-1,2-diol

Product 1

HCID 573520894-(5-Ethylpyridin-2-yl)-1,3,2lambda~4~-dioxathiolan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.98 mL (0.0387 mol) triethylamine was added to a solution of 3 g (0.017 mol) 1-(5-ethyl-pyridin-2-yl)-ethan-1,2-diol dissolved in 60 mL dichloromethane at 0-5° C. To this 1.43 mL (0.019 mol) thionyl chloride was added drop wise in 15 min. and stirring was continued for 1 hr. Reaction mixture was quenched with 10% sodium bicarbonate solution. Product was extracted with dichloromethane, which was concentrated in vacuo to obtain titled product. Yield of the product was 3.44 g (90%).

Workup

  1. customReaction mixture
  2. customwas quenched with 10% sodium bicarbonate solution
  3. extractionProduct was extracted with dichloromethane, which
  4. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-c08471176cc34e89a231b766a15d986e
Source dataset
uspto-grants-2013_05
Patent number
US08445685B2

Reaction notes

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