Water → 2-(2,6-Dimethylphenyl)thio-5-methyl-1,3,4-oxadiazole

HRID 1379089Notes

Reaction equation

HRID 1379089 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[SH:11].[CH3:12][C:13]1[O:17][C:16](C=S=O)=[N:15][N:14]=1.O>CN(C=O)C>[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[S:11][C:16]1[O:17][C:13]([CH3:12])=[N:14][N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 610452,6-DimethylthiophenolHCID 229096495-Methyl-2-sulfinylmethyl-1,3,4-oxadiazole

Product 1

HCID 229096302-(2,6-Dimethylphenyl)thio-5-methyl-1,3,4-oxadiazoleYield 49.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an NaH slurry (0.15 g, 0.0037 mol, 60% in oil) in dry DMF (5 ml) under a N2 atmosphere was added 2,6-dimethylthiophenol (0.50 ml, 0.00374 mol). The mixture was stirred for 10 min at rt and cooled to 0° C. To the cooled solution was added dropwise via syringe a solution of 5-methyl-2-sulfinylmethyl-1,3,4-oxadiazole (77) (0.5 g, 0.0034 mol) in dry DMF (1.5 ml). The mixture was stirred for 1 h, water was added (15 ml) and the aqueous layer extracted with Et2O (4×20 ml). The combined extracts were washed with water (2×25 ml), saturated NaCl solution (1×25 ml), dried (MgSO4) and solvent removed in vacuo. Chromatography on silica gel using 1/2 ethyl acetate/hexanes gave 2-(2,6-dimethylphenyl)thio-5-methyl-1,3,4-oxadiazole (24) as a white solid (0.372 g, 46%, mp 53°-54° C.).

Workup

  1. temperaturecooled to 0° C
  2. stirringThe mixture was stirred for 1 h
  3. extractionthe aqueous layer extracted with Et2O (4×20 ml)
  4. washThe combined extracts were washed with water (2×25 ml), saturated NaCl solution (1×25 ml)
  5. dry with materialdried (MgSO4) and solvent
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-c9d878b07da4443090c8c1bee4487673
Source dataset
uspto-grants-1997_09
Patent number
US05670526

Reaction notes

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