Thioxanthone → HCID 23035009, compound

HRID 1172032Notes

Reaction equation

HRID 1172032 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15]1[C:28]2[C:27](=[O:29])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[S:20][C:19]=2[CH:18]=[CH:17][CH:16]=1.[F:30][C:31]([F:44])([F:43])[S:32]([O:35]S(C(F)(F)F)(=O)=O)(=[O:34])=[O:33]>ClCCl>[F:30][C:31]([F:44])([F:43])[S:32]([O-:35])(=[O:34])=[O:33].[C:9]1([S+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[CH:17]=[CH:18][C:19]3[S:20][C:21]4[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:27](=[O:29])[C:28]=3[CH:15]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 10295ThioxanthoneHCID 13679Diphenyl sulfoxideHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 23035009HCID 23035009, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 320 ml of dichloromethane were suspended 20.2 g (0.1 mol) of diphenylsulfoxide and 21.2 g (0.1 mol) of thioxanthene-9-one, and 28.2 g (0.1 mol) of trifluoromethanesulfonic anhydride was added dropwise thereto at −70 to −60° C., followed by gradually warming to room temperature and reacting with stirring for 3 hours. After completion of the reaction, the obtained reaction solution was washed with water (320 ml×5 times) and the obtained dichloromethane layer was concentrated to dryness under reduced pressure. The obtained crude product was purified by column chromatography to obtain 18.6 g of objective substance as yellow glassy substance (yield: 34%).

Workup

  1. additionwas added dropwise
  2. customat −70 to −60° C.
  3. customAfter completion of the reaction
  4. customthe obtained reaction solution
  5. washwas washed with water (320 ml×5 times)
  6. concentrationthe obtained dichloromethane layer was concentrated to dryness under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by column chromatography
  9. customto obtain 18.6 g of objective substance as yellow glassy substance (yield: 34%)

Sources & evidence

ORD record
ord-4dc7b259d36a47658427fbe0e8a3728c
Source dataset
uspto-grants-2010_11
Patent number
US07833691B2

Reaction notes

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