Sodium hydride → HCID 19041129, compound

HRID 1683795Notes

Reaction equation

HRID 1683795 reaction equation
[I-].[CH3:2][S+](C)C.[H-].[Na+].[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([C:20]2[S:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]=[O:32])[N:26]=3)[N:24]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH3:19])[CH3:9]>CS(C)=O>[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([C:20]2[S:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH:31]4[CH2:2][O:32]4)[N:26]=3)[N:24]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH3:19])[CH3:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 19041012HCID 19041012, compound

Product 1

HCID 19041129HCID 19041129, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

880 mg of trimethylsulfonium iodide was added to a suspension of 172 mg of 60% sodium hydride in 15 ml of dimethyl sulfoxide. The mixture was subjected to a reaction at room temperature for 1 hour. Thereto was dropwise added a solution of 1 g of 2-(3,4-diethoxyphenyl)-4-(6-formyl-2-pyridyl)thiazole dissolved in 20 ml of dimethyl sulfoxide. The mixture was stirred overnight at room temperature. The reaction mixture was poured into 150 ml of ice water. The mixture was subjected to extraction three times with 200 ml of ethyl acetate. The ethyl acetate layer was water-washed and dried over anhydrous sodium sulfate. The solvent was removed. The residue was purified by silica gel column chromatography (elutant: n-hexane/ethyl acetate=4/1) to obtain 760 mg of 2-(3,4-diethoxyphenyl)-4-(6-oxiranyl-2-pyridyl)thiazole.

Workup

  1. customThe mixture was subjected to a reaction at room temperature for 1 hour
  2. extractionThe mixture was subjected to extraction three times with 200 ml of ethyl acetate
  3. washwashed
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. customThe residue was purified by silica gel column chromatography (elutant: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-87047e8e59c24731a4c3ffbffa401654
Source dataset
uspto-grants-1997_06
Patent number
US05639770

Reaction notes

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