3-(Difluoromethoxy)aniline → N-[3-(Difluoromethoxy)phenyl]-4-methyl-3-[4-(2,2,2-trifluoroacetyl)-1-piperazinyl]benzenesulfonamide

HRID 657487Notes

Reaction equation

HRID 657487 reaction equation
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][C:14]=1[N:23]1[CH2:28][CH2:27][N:26]([C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])[CH2:25][CH2:24]1>N1C=CC=CC=1>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:5]=[C:6]([NH:7][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:12])=[C:14]([N:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:34])[C:30]([F:33])([F:31])[F:32])[CH2:25][CH2:24]3)[CH:15]=2)(=[O:21])=[O:20])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 27741103-(Difluoromethoxy)anilineHCID 59563966HCID 59563966, compound

Product 1

HCID 59563972N-[3-(Difluoromethoxy)phenyl]-4-methyl-3-[4-(2,2,2-trifluoroacetyl)-1-piperazinyl]benzenesulfonamideYield 47.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.429 g of 3-(difluoromethoxy)-aniline (2.7 mmol) were dissolved in 5 mL of pyridine. 1 g of 4-methyl-3-[4-(2,2,2-trifluoro-acetyl)-piperazin-1-yl]-benzenesulfonylchloride (2.7 mmol) were added slowly at room temperature. After stirring for 16 h at room temperature, the reaction mixture was evaporated several times after addition of toluene. The residue was dissolved in dichloromethane and washed several times with 5% aqueous ammonium chloride. The organic phase was then washed with saturated aqueous sodium chloride, dried over sodium sulphate, filtered, and the solvent evaporated. The crude product was purified via silica gel chromatography using dichloromethane/methanol (0-5%) to yield 0.63 g of product.

Workup

  1. customthe reaction mixture was evaporated several times
  2. additionafter addition of toluene
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed several times with 5% aqueous ammonium chloride
  5. washThe organic phase was then washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customThe crude product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-6a2ff749fa604e1abaa2b5f9f2045ebc
Source dataset
uspto-grants-2011_12
Patent number
US08076326B2

Reaction notes

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