2,2,2-Trifluoroethanesulfonyl chloride → N-[2-({3-Chloro-4-[(2-methylphenyl)carbonyl]phenyl}amino)benzyl]-2,2,2-trifluoroethanesulfonamide

HRID 1797311Notes

Reaction equation

HRID 1797311 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])=[O:17])=[C:12]([Cl:25])[CH:11]=1.[F:26][C:27]([F:34])([F:33])[CH2:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[Cl:25][C:12]1[CH:11]=[C:10]([NH:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:2][NH:1][S:29]([CH2:28][C:27]([F:34])([F:33])[F:26])(=[O:31])=[O:30])[CH:15]=[CH:14][C:13]=1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])=[O:17]

Participants

4

Reactant 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 22174531(4-{[2-(Aminomethyl)phenyl]amino}-2-chlorophenyl)(2-methylphenyl)methanone

Product 1

HCID 22174499N-[2-({3-Chloro-4-[(2-methylphenyl)carbonyl]phenyl}amino)benzyl]-2,2,2-trifluoroethanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 148 (0.18 g, 0.71 mmol) was dissolved in dry pyridine (0.9 mL) and 2,2,2-trifluoroethanesulfonyl chloride (0.12 mL, 1.1 mmol) was added. The solution was stirred at room temperature for 1 h after which it was concentrated in vacuo. The oil was diluted with H2O and the water phase was extracted three times with EtOAc. The combined organic phases were washed with 10% aqueous NaHCO3, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc/petroleum ether 1:2 as the eluent to afford the title compound as a yellow oil.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionThe oil was diluted with H2O
  3. extractionthe water phase was extracted three times with EtOAc
  4. washThe combined organic phases were washed with 10% aqueous NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-e5d7ff4b78074324995318fec3a48543
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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