Ethylamine → N-ethyl-1-[4-(trifluoromethyl)phenyl]methanesulfonamide

HRID 729251Notes

Reaction equation

HRID 729251 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10](Cl)(=[O:12])=[O:11])=[CH:5][CH:4]=1.[CH2:16]([NH2:18])[CH3:17]>C1COCC1>[CH2:16]([NH:18][S:10]([CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:4][CH:5]=1)(=[O:12])=[O:11])[CH3:17]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 594332[4-(Trifluoromethyl)phenyl]methanesulfonyl chloride

Product 1

HCID 68662627N-ethyl-1-[4-(trifluoromethyl)phenyl]methanesulfonamideYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[[4-(Trifluoromethyl)phenyl]methyl]sulfonyl chloride (0.60 g, 2.32 mmol) was added dropwise to a saturated solution of ethylamine in THF (10 mL). The mixture was stirred at room temperature for 1 h. It was evaporated and the residue was dissolved in DCM and the resulting mixture was washed with 5% HCl, dried and evaporated to give the title compound (0.49 g, 79%) as a solid; 1H NMR (500 MHz, CDCl3): δ 7.68 (d, 2H), 7.55 (d, 2H), 4.32 (s, 2H), 4.01 (bs, 1H), 3.08-3.14 (m, 2H), 1.19 (t, 3H); Mass Spectrum: M−H+ 265.

Workup

  1. customIt was evaporated
  2. dissolutionthe residue was dissolved in DCM
  3. washthe resulting mixture was washed with 5% HCl
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-3512c45ad0c3455d99ab0761c04a3c80
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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