Phenol → HCID 21973812, compound

HRID 2085276Notes

Reaction equation

HRID 2085276 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15]([NH:20][CH2:21][C:22]([NH:25][C:26](=[O:28])[CH3:27])([CH3:24])[CH3:23])[C:14]([CH3:29])=[C:13]([CH3:30])[N:12]=1.CCOC(C)=O>C(COC)OC>[CH3:30][C:13]1[C:14]([CH3:29])=[C:15]([NH:20][CH2:21][C:22]([NH:25][C:26](=[O:28])[CH3:27])([CH3:24])[CH3:23])[C:16]([N+:17]([O-:19])=[O:18])=[C:11]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:12]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 21973825HCID 21973825, compound

Product 1

HCID 21973812HCID 21973812, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A 250 mL-round bottom flask was charged with NaH (60% oil dispersion, 534 mg, 13.3 mmol) under N2. The NaH was washed with three portions of hexanes and dried under a stream of N2. Dimethoxyethane (10 mL) was then added to the flask followed by phenol (1.25 g, 13.3 mmol). After stirring for 10 min, a solution of N-{2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]-1,1-dimethylethyl}acetamide (2.80 g, 8.89 mmol) in 15 mL of dimethoxyethane was added to the reaction mixture, dropwise, via cannula. The reaction mixture was then heated to reflux for 24 h. The cooled solution was then treated with 100 mL of EtOAc and washed successively with H2O, 1% Na2CO3 solution (2×), H2O and brine. The organic portion was dried with Na2SO4 and concentrated to give a brown oil. Column chromatography (SiO2, 50% EtOAc/hexanes) gave N-{2-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]-1,1-dimethylethyl}acetamide (2.40 g) as a yellow oil.

Workup

  1. washThe NaH was washed with three portions of hexanes
  2. dry with materialdried under a stream of N2
  3. additionDimethoxyethane (10 mL) was then added to the flask
  4. temperatureThe reaction mixture was then heated
  5. temperatureto reflux for 24 h
  6. washwashed successively with H2O, 1% Na2CO3 solution (2×), H2O and brine
  7. dry with materialThe organic portion was dried with Na2SO4
  8. concentrationconcentrated
  9. customto give a brown oil

Sources & evidence

ORD record
ord-21de6ffa892748daa1962c67bbf8f7c8
Source dataset
uspto-grants-2004_04
Patent number
US06720333B2

Reaction notes

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