Toluene → HCID 86676053, compound

HRID 2281026Notes

Reaction equation

HRID 2281026 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([N:10]1[C:14](=O)[CH2:13][O:12][C:11]1=[S:16])[CH3:9].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C(OCC)(=O)C>[CH2:8]([N:10]1[C:14](=[S:26])[CH2:13][O:12][C:11]1=[S:16])[CH3:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 827344-Oxazolidinone, 3-ethyl-2-thioxo-HCID 87949Lawesson's reagent

Product 1

HCID 86676053HCID 86676053, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A toluene (10 mL) solution of 3-ethyl-2-thioxooxazolidin-4-one 3 (145 mg, 1.0 mmol) and Lawesson's reagent (607 mg, 1.5 mmol) was refluxed overnight. The solution was cooled and diluted with ethyl acetate (100 mL), then washed with water (2×20 mL). The organic layer was dried with brine and MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=10:1), and the desired product 6 was obtained in 94% yield (152 mg, orange oil). 1H NMR (400 MHz, CDCl3): δ 5.12 (s, 2H), 4.21 (q, J=7.2 Hz, 2H), 1.29 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureThe solution was cooled
  2. washwashed with water (2×20 mL)
  3. dry with materialThe organic layer was dried with brine and MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-8bb58e0547b24dec9ac5742aabb265a0
Source dataset
uspto-grants-2015_09
Patent number
US09139575B2

Reaction notes

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