Lawesson's reagent → HCID 86650251, compound

HRID 81527Notes

Reaction equation

HRID 81527 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:15][F:16])[NH:13][C:12](=O)[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:15][F:16])[NH:13][C:12](=[S:26])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 66665880HCID 66665880, compound

Product 1

HCID 86650251HCID 86650251, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-(3-bromo-phenyl)-5-fluoromethyl-morpholin-3-one (1.52 g, 5.28 mmol) and Lawesson's reagent (2.14 g, 5.28 mmol) in 21 ml of THF was heated at 50° C. for 1 h and then evaporated. The residue was chromatographed on silica gel (cyclohexane/EtOAc=15:1) to give the title compound in the form of a colourless foam. TLC (hexane/EtOAc=3:1): Rf=0.21; HPLC: RtH2=3.49 min; 1H-NMR (400 MHz, CD3OD): 7.65 (s, 1H), 7.58 (d, 1H), 7.47 (d, 1H), 7.39 (t, 1H), 4.87 (s, 2H), 4.63 (d, 1H), 4.50 (s, 2H), 4.02 (d, 1H); MS: 304, 306 [(M+H)+].

Workup

  1. customevaporated
  2. customThe residue was chromatographed on silica gel (cyclohexane/EtOAc=15:1)

Sources & evidence

ORD record
ord-ab3cac00a9e449fb97038cc73257fada
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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