Dimethylformamide → HCID 22251491, compound

HRID 1180813Notes

Reaction equation

HRID 1180813 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(S(NN)(=O)=[O:24])C=CC=CC=1.CN([CH:31]=[O:32])C>>[O:10]=[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][C:4]([C:31]([OH:32])=[O:24])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7189CinnamoylbenzeneHCID 65723Benzenesulfonyl hydrazide

Product 1

HCID 22251491HCID 22251491, compoundYield 31%

Conditions

Temperature
10 °C

Procedure

To a stirred solution at room temperature of chalcone XXIIIa (1.29 g, 5.13 mmol) in DMF (20 ml) was added phenylsulfonylhydrazine (1.76 g, 10.26 mmol). The reaction mixture was stirred at 10° C. for 15 h, cooled and concentrated. The remained oily residue was partitioned between a saturated aqueous solution of NH4Cl and AcOEt. After separation, the organic layer was dried, partially evaporated and filtered. The filtrate was purified by flash chromatography on silica gel (AcOEt/hexane:50/50□75/25) to form a material which after a second column purification (MeOH/CH2Cl2:5/95) afford the title compound XXVIa (400 mg, 1.59 mmol, 31% yield).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe remained oily residue was partitioned between a saturated aqueous solution of NH4Cl and AcOEt
  4. customAfter separation
  5. customthe organic layer was dried
  6. custompartially evaporated
  7. filtrationfiltered
  8. customThe filtrate was purified by flash chromatography on silica gel (AcOEt/hexane:50/50□75/25)
  9. customto form a material which
  10. customafter a second column purification (MeOH/CH2Cl2:5/95)

Sources & evidence

ORD record
ord-4e3bb493536b462bbd8696117c8e9a66
Source dataset
uspto-grants-2007_10
Patent number
US07282608B2

Reaction notes

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