Phenol → HCID 21913050, compound

HRID 1352529Notes

Reaction equation

HRID 1352529 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].Cl[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:16]([CH3:32])=[C:15]([CH3:33])[N:14]=1>COCCOCCOC>[CH3:33][C:15]1[C:16]([CH3:32])=[C:17]([NH:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:18]([N+:19]([O-:21])=[O:20])=[C:13]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:14]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 21913573HCID 21913573, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21913050HCID 21913050, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Methoxyethyl ether (diglyme) (3 ml) and sodium hydride (60% in oil) (0.56 g) were combined and cooled to 0° C. Phenol (1.24 g) was added slowly in portions to allow for controlled release of hydrogen gas. A solution of 2-chloro-5,6-dimethyl-3-nitro-N-(2-phenoxyethyl)pyridin-4-amine (4.00 g) and diglyme (37 ml) was then added and the reaction mixture was heated to 150° C. for 16 hours. At this time, the reaction stalled at 85% completion. The reaction mixture was allowed to cool and the solvent was removed under reduced pressure. The oil was dissolved in ethyl acetate, washed with water, dried with magnesium sulfate, and concentrated under reduced pressure. The product was run through a column using 20/80 ethyl acetate/hexane as the eluant. HPLC analysis of the resulting orange solid indicated sufficient purity for use in the next step.

Workup

  1. temperaturethe reaction mixture was heated to 150° C. for 16 hours
  2. temperatureto cool
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe oil was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-307e48ee44314f1b996c716bc74ed6ae
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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