Sodium Acetate → HCID 58092097, compound

HRID 1873476

Reaction equation

HRID 1873476 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].Br[CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]([NH:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[O:19])=[CH:10][CH:9]=1>CN(C=O)C.COC(C)(C)C>[C:1]([O:4][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18](=[O:19])[NH:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 580920724-(bromomethyl)-N-[(trimethylsilyl)methyl]naphthalene-1-carboxamide

Product 1

HCID 58092097HCID 58092097, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A mixed solution of sodium acetate (1.1 g), 4-(bromomethyl)-N-[(trimethylsilyl)methyl]naphthalen-1-carboxamide (2.5 g) in DMF (30 ml) was stirred for 3 hours at 70° C. The reaction mixture was returned to room temperature and diluted with t-butyl methyl ether. The mixture was washed with water and a saturated aqueous brine, subsequently dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain (4{[(trimethylsilyl)methyl]carbamoyl}naphthalen-1-yl)methyl acetate (1.3 g).

Workup

  1. customwas returned to room temperature
  2. washThe mixture was washed with water
  3. dry with materiala saturated aqueous brine, subsequently dried over magnesium sulfate
  4. filtrationAfter filtering the reaction mixture
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe resulting mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6e07930c18cb41739054c5be1c4588c6
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Linked notes

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