Dimethylformamide → HCID 22998474, compound

HRID 252250Notes

Reaction equation

HRID 252250 reaction equation
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].CN(C=O)C.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:15][CH:14]=1>>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[S:20][C:21]([S:1]([Cl:5])(=[O:3])=[O:2])=[CH:22][CH:23]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24648Sulfuryl chlorideHCID 27694252-(4-methoxyphenyl)thiophene

Product 1

HCID 22998474HCID 22998474, compound

Conditions

Temperature
100 °C

Procedure

Sulfuryl chloride (0.32 g, 2.34 mmol) was added dropwise a stirred solution of dry DMF (0.18 ml, 2.34 mmol) at 0° C. under an argon atmosphere resulting in the formation of a white solid. After 15 min, 2-(4-methoxy-phenyl)-thiophene (0.38 g, 2 mmol) was added and the mixture was warmed to 100° C. and the melt was further stirred for 45 min. Crushed ice was added and the reaction mixture was extracted with ethyl acetate (2×) and the combined organic extracts were washed with water, brine, dried (MgSO4.2H2O) filtered and concentrated under reduced pressure. The crude, green solid was purified over silica gel (ethyl acetate/n-heptane 1:9): green solid, 0.13 g (18%).

Workup

  1. customresulting in the formation of a white solid
  2. additionCrushed ice was added
  3. extractionthe reaction mixture was extracted with ethyl acetate (2×)
  4. washthe combined organic extracts were washed with water, brine
  5. dry with materialdried (MgSO4.2H2O)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude, green solid was purified over silica gel (ethyl acetate/n-heptane 1:9)

Sources & evidence

ORD record
ord-4ca3d112d1dc4698b6e37b626f81e666
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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