Ethyl Acetate → 5-(3-Bromophenyl)-5-methyl-3-morpholinethione

HRID 81515Notes

Reaction equation

HRID 81515 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[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:25])=CC=1.CCOC(C)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[NH:13][C:12](=[S:25])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 581553055-(3-Bromophenyl)-5-methylmorpholin-3-one

Product 1

HCID 726812675-(3-Bromophenyl)-5-methyl-3-morpholinethione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(3-bromo-phenyl)-5-methyl-morpholin-3-one (18 g, 67 mmol) in dry THF was treated with Lawesson's reagent (27 g, 67 mmol) in one portion at room temperature. The mixture was refluxed for 2 h. The title compound was obtained by chromatography on silica gel (PE/EtOAc=30:1 to 10:1). 1H-NMR (400 MHz, DMSO-d6): 11.08 (s, 1H), 7.50 (m, 2H), 7.35 (m, 2H), 4.36 (s, 2H), 4.00 (m, 1H), 3.73 (m, 1H), 1.51 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 2 h

Sources & evidence

ORD record
ord-25004a1c29b941b49238d9e6107d23c0
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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