Triethylamine → N-[4-(Difluoromethoxy)benzyl]-1-phenylmethanesulfonamide

HRID 729260Notes

Reaction equation

HRID 729260 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH2:20]([S:27](Cl)(=[O:29])=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[F:1][CH:2]([F:12])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][S:27]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:29])=[O:28])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 20633524-(Difluoromethoxy)benzylamine

Product 1

HCID 33038515N-[4-(Difluoromethoxy)benzyl]-1-phenylmethanesulfonamideYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-(Difluoromethoxy)benzyl amine (1.73 g, 9.97 mmol) was dissolved in THF (10 mL). It was cooled in an ice-bath. Under nitrogen atmosphere, triethylamine (1.46 mL, 10.46 mmol) was added and then benzylsulfonyl chloride (1.9 g, 9.97 mmol) in THF (10 mL) was dropped in. The cooling bath was removed after the addition. The mixture was stirred for 3 h and then evaporated to dryness. DCM (50 mL) was added to the residue. It was then washed with 1% HCl (15 mL), water (50 mL×3) and brine, dried (MgSO4) and evaporated to give the title compound (3.01 g. 92%) as a solid; 1H NMR (400 MHz, CDCl3): δ 7.32-7.40 (m, 5H), 7.26 (d, 2H), 7.09 (d, 2H), 6.49 (t, 1H), 4.36 (bt, 1H), 4.24 (s, 2H), 4.10 (d, 2H); Mass Spectrum: M−H+ 326.

Workup

  1. temperatureIt was cooled in an ice-bath
  2. customThe cooling bath was removed
  3. additionafter the addition
  4. customevaporated to dryness
  5. additionDCM (50 mL) was added to the residue
  6. washIt was then washed with 1% HCl (15 mL), water (50 mL×3) and brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-96e07fbadc31472abab737d3795488c5
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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