Lawesson's reagent → (S)-2'-bromo-7'-iodospiro[morpholine-3,9'-xanthene]-5-thione

HRID 455627Notes

Reaction equation

HRID 455627 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([I:16])=[CH:9][CH:10]=3)[C@:5]3([CH2:21][O:20][CH2:19][C:18](=O)[NH:17]3)[C:4]=2[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([I:16])=[CH:9][CH:10]=3)[C@:5]3([CH2:21][O:20][CH2:19][C:18](=[S:32])[NH:17]3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67439034(S)-2'-bromo-7'-iodospiro[morpholine-3,9'-xanthen]-5-one

Product 1

HCID 86658380(S)-2'-bromo-7'-iodospiro[morpholine-3,9'-xanthene]-5-thioneYield 130.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 250-mL flask, the (S)-2′-bromo-7′-iodospiro[morpholine-3,9′-xanthen]-5-one (1.483 g, 3.14 mmol) was suspended in toluene (30 mL). Lawesson's reagent (0.794 g, 1.963 mmol) was added. An air-cooled condenser was affixed, and the reaction vessel was placed in a 90° C. oil bath. After 7 h, the reaction was concentrated. Without working it up, the residue was purified by chromatography (15% EtOAc/hexanes) to afford (S)-2′-bromo-7′-iodospiro[morpholine-3,9′-xanthene]-5-thione (1.25 g, 2.56 mmol).

Workup

  1. customAn air-cooled condenser was affixed
  2. customwas placed in a 90° C.
  3. concentrationthe reaction was concentrated
  4. customthe residue was purified by chromatography (15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-abb547f625054a11aec75f3e007a8520
Source dataset
uspto-grants-2013_07
Patent number
US08497264B2

Reaction notes

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