Sodium hydride → N-t-butyldimethylsilylphenoxazine

HRID 1381654Notes

Reaction equation

HRID 1381654 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>O1CCCC1.CN(C)C=O>[Si:17]([N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 67278Phenoxazine

Product 1

HCID 14031259N-t-butyldimethylsilylphenoxazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

5 Grams of phenoxazine was dissolved in 100 ml of dry tetrahydrofuran, then 1.63 g of 50% sodium hydride in mineral oil was added and the mixture refluxed for 30 minutes. Then 6.19 g of t-butyldimethylsilyl chloride in dimethylformamide (2 ml) and tetrahydrofuran (8 ml) was added and reflux was continued for five more minutes. The reaction was quenched by the addition of water, the organic layer was separated and dried over sodium sulfate. Then the solvent was removed under reduced pressure and the residue purified by column chromatography (silica as solid phase, hexane:ethylacetate (95:5) as mobile phase). N-t-butyldimethylsilylphenoxazine had a melting point of 57° C. after crystallization from pentane.

Workup

  1. temperaturethe mixture refluxed for 30 minutes
  2. temperaturereflux
  3. customThe reaction was quenched by the addition of water
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customThen the solvent was removed under reduced pressure
  7. customthe residue purified by column chromatography (silica as solid phase, hexane:ethylacetate (95:5) as mobile phase)
  8. customafter crystallization from pentane

Sources & evidence

ORD record
ord-7dbf161c541e442ea0af95eb6b7f7196
Source dataset
uspto-grants-1989_02
Patent number
US04803269

Reaction notes

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