Methanol → HCID 12115479, compound

HRID 2373330Notes

Reaction equation

HRID 2373330 reaction equation
[Na].[CH3:2][CH:3]([C:8]1[CH:14]=[C:13]([C:15](F)([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:11][C:9]=1[NH2:10])[CH2:4][CH:5]([CH3:7])[CH3:6].[CH3:25][OH:26]>>[CH3:2][CH:3]([C:8]1[CH:14]=[C:13]([C:15]([O:26][CH3:25])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:11][C:9]=1[NH2:10])[CH2:4][CH:5]([CH3:7])[CH3:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 22734601HCID 22734601, compound

Product 1

HCID 12115479HCID 12115479, compoundYield 87%

Procedure

Sodium (533 mg, 23 mmol) was dissolved in methanol (40 ml), followed by adding thereto 2-(1,3-dimethylbutyl)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline (2 g, 5.8 mmol), and the resulting mixture was stirred at reflux temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure, and the resulting residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain 1.8 g of the desired compound.

Workup

  1. additionby adding
  2. temperatureat reflux temperature for 3 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting residue was separated
  9. custompurified by silica gel column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-ebd400bea03b4d0297a43ecc61135d6c
Source dataset
uspto-grants-2008_12
Patent number
US07459477B2

Reaction notes

Loading…