Lawesson's reagent → (R)-5-(3-Bromo-5-nitro-phenyl)-5-methyl-morpholine-3-thione

HRID 2196247Notes

Reaction equation

HRID 2196247 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:11]2([CH3:18])[NH:16][C:15](=O)[CH2:14][O:13][CH2:12]2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]([C@@:11]2([CH3:18])[NH:16][C:15](=[S:28])[CH2:14][O:13][CH2:12]2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 66666034HCID 66666034, compound

Product 1

HCID 86667520(R)-5-(3-Bromo-5-nitro-phenyl)-5-methyl-morpholine-3-thione

Procedure

(R)-5-(3-Bromo-5-nitro-phenyl)-5-methyl-morpholin-3-one (2.60 g, 7.84 mmol) and Lawesson's reagent (2.54 g, 6.27 mmol) were stirred at 80° C. for 2 hrs. Volatiles were removed under reduced pressure and the crude product mixture was purified by automated column chromatography (cyclohexane/ethyl acetate) yielding the title compound as yellow foam. 1H-NMR (360 MHz, DMSO-d6): 11.28 (1H, NH), 8.38 (s, 1H), 8.22 (s, 1H), 8.17 (s, 1H), 4.44 (m, 1H), 4.22 (d, 1H), 3.81 (m, 1H), 1.60 (s, 3H); MS: 331 [(M+H)+].

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe crude product mixture was purified by automated column chromatography (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-b3d505cfe55b41f287ef6c7ff262401e
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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