4-Oxazolidinone, 3-ethyl-2-thioxo- → HCID 76046593, compound

HRID 2281025Notes

Reaction equation

HRID 2281025 reaction equation
[CH2:1]([N:3]1[C:7](=[O:8])[CH2:6][O:5][C:4]1=[S:9])[CH3:2].[C:10]1([C:16]2[O:20][C:19]([CH:21]=O)=[CH:18][CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH2:1]([N:3]1[C:7](=[O:8])[C:6](=[CH:21][C:19]2[O:20][C:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:17][CH:18]=2)[O:5][C:4]1=[S:9])[CH3:2]

Participants

5

Reactant 3

HCID 827344-Oxazolidinone, 3-ethyl-2-thioxo-HCID 517045Sodium AcetateHCID 27694205-Phenyl-2-furaldehyde

Product 1

HCID 76046593HCID 76046593, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 3-ethyl-2-thioxooxazolidin-4-one 3 (145 mg, 1.0 mmol), 5-phenyl-2-furaldehyde 4 (172 mg, 1.0 mmol) and sodium acetate (410 mg, 5.0 mmol) was added acetic acid (5 mL). The reaction mixture was refluxed for 30 h, then the excess solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), then washed with water (2×20 mL). The organic layer was dried with brine and MgSO4, then concentrated in vacuo. The desired product 5 (JL101) was obtained by recrystallization from an ethyl acetate/hexanes mixture in 45% yield (135 mg, light yellow needles). 1H NMR (400 MHz, CDCl3): 7.81-7.76 (m, 2H), 7.44 (dt, J=8.0, 1.6 Hz), 7.36 (t, J=6.0 Hz, 1H), 7.28 (d, J=3.6 Hz, 1H), 6.88 (d, J=3.6 Hz, 1H), 6.80 (s, 1H), 3.97 (q, J=7.2 Hz, 2H), 1.34 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 30 h
  2. customthe excess solvent was removed in vacuo
  3. additionThe residue was diluted with ethyl acetate (100 mL)
  4. washwashed with water (2×20 mL)
  5. dry with materialThe organic layer was dried with brine and MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75d221542ca44c3aa33b4274858e4773
Source dataset
uspto-grants-2015_09
Patent number
US09139575B2

Reaction notes

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