Acetonitrile → (R)-4-(5-chloro-6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

HRID 2389157Notes

Reaction equation

HRID 2389157 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.C(#N)C.[Cl:22]N1C(=O)CCC1=O>>[Cl:22][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)=[CH:8]2

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 31398ChlorosuccinimideHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67415649(R)-4-(5-chloro-6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-oneYield 87.7%

Conditions

Temperature
80 °C

Procedure

(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (0.5895 g, 0.002423 mol) was suspended in acetonitrile (3.37 mL, 0.0646 mol) in a 40 mL vial equipped with a magnetic stir bar. N-Chlorosuccinimide (0.356 g, 0.00266 mol) was added and the mixture was heated at 80° C. After 2 hours, HPLC analysis showed that the reaction was complete. The mixture was cooled to room temperature and filtered. The residue was washed with acetonitrile, azeotroped with toluene then dried under vacuum and collected to give 590 mg of the title compound (62% yield).

Workup

  1. customvial equipped with a magnetic stir bar
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. washThe residue was washed with acetonitrile
  5. customazeotroped with toluene
  6. customthen dried under vacuum
  7. customcollected

Sources & evidence

ORD record
ord-151e07605177480dbf05d31ff32830cb
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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