Sodium hydride → HCID 54397840, compound

HRID 2372319Notes

Reaction equation

HRID 2372319 reaction equation
[H-].[Na+].[Cl-].[CH3:4][S+](C)(C)=O.[F:9][C:10]([F:25])([F:24])[C:11]1[N:16]=[C:15]([N:17]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[CH:14]=[CH:13][N:12]=1>CS(C)=O>[F:25][C:10]([F:9])([F:24])[C:11]1[N:16]=[C:15]([N:17]2[CH2:22][CH2:21][C:20]3([O:23][CH2:4]3)[CH2:19][CH2:18]2)[CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 197819Trimethyloxosulphonium chlorideHCID 53886506HCID 53886506, compound

Product 1

HCID 54397840HCID 54397840, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Sodium hydride (0.48 g of 60% mineral oil dispersion, 12 mmol) in a round bottom flask was washed free of the mineral oil with hexanes before DMSO (20 mL, distilled from calcium hydride) was added. Trimethyloxosulfonium chloride (1.54 g, 12 mmol) was added and the mixture was stirred under dry nitrogen for 20 min at room temperature. A solution of XXVIII (2.45 g, 10 mmol) in DMSO (5 mL) was then added to this milky suspension. The mixture was stirred at room temperature for 30 min, and then heated in a 50° C. oil bath for 1 hr. The reaction was quenched with water (30 mL) and extracted with ether (3×60 mL). The ether extracts were washed with water (3×15 mL), dried over sodium sulfate, and concentrated in vacuo to give the product as a white solid (2.1 g, 81%).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. temperatureheated in a 50° C. oil bath for 1 hr
  4. customThe reaction was quenched with water (30 mL)
  5. extractionextracted with ether (3×60 mL)
  6. washThe ether extracts were washed with water (3×15 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e040173b2dec495ea8adbb44d93e4261
Source dataset
uspto-grants-1992_03
Patent number
US05098904

Reaction notes

Loading…