Dimethylformamide → 5-[3-Chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]-1,3-oxazolidin-2-one

HRID 1499949Notes

Reaction equation

HRID 1499949 reaction equation
N1C(Cl)=NC(Cl)=NC=1[Cl:3].CN(C)C=O.[Cl:15][C:16]1[C:17]([CH3:33])=[C:18]([CH:27]2[O:31][C:30](=[O:32])[NH:29][CH2:28]2)[C:19]([O:25][CH3:26])=[C:20]([CH:22](O)[CH3:23])[CH:21]=1.S(Cl)(Cl)=O>C(Cl)Cl>[Cl:15][C:16]1[C:17]([CH3:33])=[C:18]([CH:27]2[O:31][C:30](=[O:32])[NH:29][CH2:28]2)[C:19]([O:25][CH3:26])=[C:20]([CH:22]([Cl:3])[CH3:23])[CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7954Cyanuric chlorideHCID 24386Thionyl ChlorideHCID 866778645-[3-Chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]-1,3-oxazolidin-2-one

Product 1

HCID 866778655-[3-Chloro-5-(1-chloroethyl)-6-methoxy-2-methylphenyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of cyanuric chloride (16 mg, 0.084 mmol) and N,N-dimethylformamide (15 μL) was stirred at room temperature for 10 minutes. A solution of 5-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]-1,3-oxazolidin-2-one (16 mg, 0.056 mmol) (racemic mixture of two diastereomers from step 2) in methylene chloride (0.3 mL) was added and the reaction was stirred at room temperature overnight. Thionyl chloride (12 μL, 0.17 mmol) was added and stirred for 10 min. The mixture was diluted with methylene chloride, washed with saturated sodium bicarbonate, water, brine, dried over sodium sulfate, filtered and concentrated to give the desired compound as a racemic mixture of two diastereomers, 17 mg, 100%. LCMS calculated for C13H16Cl2NO3 (M+H)+: m/z=304.0; found: 304.1.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. stirringstirred for 10 min
  3. washwashed with saturated sodium bicarbonate, water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fbd52518c7814a3aa44b3c682e796425
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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