Dimethyl Sulfoxide → HCID 66919222, compound

HRID 1175196Notes

Reaction equation

HRID 1175196 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2=[CH:9][S:10][CH:11]=[C:6]2[O:5][CH2:4]1.[C:12]([O-:20])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH4+].CS(C)=O>O>[C:12]([O:20][CH2:2][CH:3]1[CH2:4][O:5][C:6]2=[CH:11][S:10][CH:9]=[C:7]2[O:8]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 15830Ammonium benzoateHCID 569236862-(Bromomethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine

Product 1

HCID 66919222HCID 66919222, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 100 mL round bottom flask 9.00 g (0.0382 mol) 2-(bromomethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine, 6.39 g (0.0459 mol) ammonium benzoate, and 55 g DMSO were combined. A reflux condenser was equipped and the reaction was heated to 100 C overnight. After cooling to room temperature, the reaction mixture was poured into water and the product was extracted with methylene chloride. The organic fractions were combined and the solvent removed under reduced pressure. Purification by column chromatography provided 7.5 g (71% yield) of a white solid whose structure was confirmed by 1H/13C NMR and LC-MS.

Workup

  1. customA reflux condenser was equipped
  2. temperaturethe reaction was heated to 100 C overnight
  3. extractionthe product was extracted with methylene chloride
  4. customthe solvent removed under reduced pressure
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-008a9b8533e94cc98d395366932fb97d
Source dataset
uspto-grants-2010_11
Patent number
US07838688B2

Reaction notes

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