Imidazole → HCID 69364312, compound

HRID 723783Notes

Reaction equation

HRID 723783 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[CH3:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:20][C@H:19]([CH2:21]OS(C)(=O)=O)[O:18][C:17]2=[O:27])=[CH:12][CH:11]=1>CN(C)C=O.O>[CH3:8][S:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH2:20][C@H:19]([CH2:21][N:3]3[CH:7]=[CH:6][N:5]=[CH:4]3)[O:18][C:17]2=[O:27])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 87799035HCID 87799035, compound

Product 1

HCID 69364312HCID 69364312, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (80% in oil, 23 mg, 0.77 mM) was stirred under nitrogen in N,N-dimethylformamide (5 ml), imidazole (52 mg, 0.77 mM) added, and stirring continued for 10 minutes. (5R)-3-(4-Methylthiophenyl)-5-methanesulfonyloxymethyloxazolidin-2-one (200 mg, 0.63 mM) was dissolved in N,N-dimethylformamide (5 ml), added to the above, and the mixture stirred 18 hours at ambient temperature. After diluting with water (30 ml), the mixture was extracted with ethyl acetate (30 ml), the extract washed with brine (25 ml), dried (magnesium sulfate) and evaporated. The residue was triturated with diethyl ether, and filtered to give the desired product (129 mg, mp 129–131°).

Workup

  1. additionadded to the above, and the mixture
  2. stirringstirred 18 hours at ambient temperature
  3. extractionthe mixture was extracted with ethyl acetate (30 ml)
  4. washthe extract washed with brine (25 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customThe residue was triturated with diethyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-18321f2ba806452ab1d69c7c96c78570
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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