Sodium hydride → N-{2-t-Butyl-5-[2-(oxiran-2-yl)ethyl]phenyl}-2-(9H-xanthen-9-yl)acetamide

HRID 1734923Notes

Reaction equation

HRID 1734923 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]=[O:22])=[CH:15][C:14]=1[NH:23][C:24](=[O:40])[CH2:25][CH:26]1[C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[O:33][C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)([CH3:12])([CH3:11])[CH3:10]>O1CCCC1.C(OCC)(=O)C>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]2[CH2:4][O:22]2)=[CH:15][C:14]=1[NH:23][C:24](=[O:40])[CH2:25][CH:26]1[C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[O:33][C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 19966225HCID 19966225, compound

Product 1

HCID 19966191N-{2-t-Butyl-5-[2-(oxiran-2-yl)ethyl]phenyl}-2-(9H-xanthen-9-yl)acetamideYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 690 mg (15.8 mmol) of sodium hydride (as a 55% w/w dispersion in mineral oil, which had previously been washed with hexane) in 10 ml of dimethyl sulfoxide was stirred for 30 minutes, after which 2.66 g (12.1 mmol) of trimethylsulfoxonium iodide were added. The resulting mixture was stirred for 1 hour at 40° C., and then a solution of 4.50 g (10.5 mmol) of N-[2-t-butyl-5-(3-oxopropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 19) in 25 ml of tetrahydrofuran was added dropwise over a period of 5 minutes. The reaction mixture was then stirred for 1 hour, after which the reaction mixture was cooled to room temperature and then diluted with ethyl acetate. The diluted mixture was washed several times with water and once with a saturated aqueous solution of sodium chloride. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 250 g of silica gel, using a 9:1 by volume mixture of methylene chloride and ethyl acetate as the eluent, to give 3.00 g (yield 65%) of the title compound as crystals, melting at 156°-157° C. (after recrystallization from a mixture of ethyl acetate and hexane).

Workup

  1. washhad previously been washed with hexane) in 10 ml of dimethyl sulfoxide
  2. stirringThe resulting mixture was stirred for 1 hour at 40° C.
  3. stirringThe reaction mixture was then stirred for 1 hour
  4. washThe diluted mixture was washed several times with water
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through 250 g of silica gel
  8. additionby volume mixture of methylene chloride and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-fd769c58a66941cbb5f924a13b88321a
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

Loading…