Dimethylformamide → HCID 12218100, compound

HRID 1899733Notes

Reaction equation

HRID 1899733 reaction equation
[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C=O)C.[S:20](Cl)([Cl:23])(=[O:22])=[O:21]>>[C:1]1([C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:8][S:20]([Cl:23])(=[O:22])=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 107401,1-DiphenylethyleneHCID 24648Sulfuryl chloride

Product 1

HCID 12218100HCID 12218100, compoundYield 29%

Conditions

Temperature
90 °C

Procedure

1,1-Diphenylethene (11.3 mmol, 2 ml) was added to a solution of DMF (22.7 mmol, 1.75 ml) and sulfuryl chloride (19.3 mmol, 1.55 ml) at 0° C. The reaction was heated to 90° C. for 4 hr, then cooled to ambient temperature and poured into ice (500 ml). The aqueous layer was extracted with EtOAc (2×100 ml). Then the organic was dried (MgSO4) filtered and concentrated. Flash chromatography (5% EtOAc/hexane) provided 0.92 g (29% yield) of light yellow crystals.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionThe aqueous layer was extracted with EtOAc (2×100 ml)
  3. dry with materialThen the organic was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customFlash chromatography (5% EtOAc/hexane) provided 0.92 g (29% yield) of light yellow crystals

Sources & evidence

ORD record
ord-b0900369af114a5796d1a1ca84a02359
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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