Dimethyl Sulfoxide → HCID 58477277, compound

HRID 876530Notes

Reaction equation

HRID 876530 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:21])/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].II.CS(C)=O>O1CCOCC1>[N+:8]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:2]=1[O:1][C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])=[CH:12][C:11]2=[O:21])([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 807IodineHCID 58477233HCID 58477233, compound

Product 1

HCID 58477277HCID 58477277, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (E)-1-(2-hydroxy-3-nitrophenyl)-3-o-tolylprop-2-en-1-one 21 (250 mg, 0.88 mmol), I2 (471 mg, 1.86 mmol), DMSO (0.5 ml) and 1,4-dioxane (10 ml) was heated at reflux for 5 h. The reaction mixture was concentrated and H2O was added. The resulting precipitate was collected by filtration, rinsed with pentane/EtOAc (1:1) and dried under vacuum to give 22 as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. concentrationThe reaction mixture was concentrated
  4. additionH2O was added
  5. filtrationThe resulting precipitate was collected by filtration
  6. washrinsed with pentane/EtOAc (1:1)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-497b40f2b0a44534a5de17f87581a5de
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

Loading…