Acetone → HCID 28449673, compound

HRID 343162Notes

Reaction equation

HRID 343162 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[CH3:13][C:14]([CH3:16])=O.[Na]>ClCCCl>[CH:14]([NH:8][C:7]1[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=1)([CH3:16])[CH3:13]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6008484-(Trifluoromethoxy)anilineHCID 5360545Sodium

Product 1

HCID 28449673HCID 28449673, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 9.33 g of p-trifluoromethoxyaniline, 4.1 mL of acetone, and 14.53 g of sodium triacetoxyborohydryde in 50 mL of 1,2-dichloroethane were stirred overnight at RT. The reaction mixture is then poured onto ice-water and product extracted with 100 mL of dichloromethane. The organic layer is washed with water, sat NaHCO3, dried with Na2SO4 and solvent evaporated to afford 12 g of Isopropyl-(4-trifluoromethoxy-phenyl)-amine: 1H NMR (300 MHz, CDCl3) δ7.06 (d, 2H, J=8.5), 6.56 (d, 2H, J=8.5), 3.63(m, 1H), 1.25 (d, 6H, J=6.8).

Workup

  1. additionThe reaction mixture is then poured onto ice-water and product
  2. extractionextracted with 100 mL of dichloromethane
  3. washThe organic layer is washed with water
  4. dry with materialdried with Na2SO4 and solvent
  5. customevaporated

Sources & evidence

ORD record
ord-0e8b57d32fa44ed9aaed8f9983679da8
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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