Butylamine → N-butyl-1-(4-chlorophenyl)methanesulfonamide

HRID 729254Notes

Reaction equation

HRID 729254 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][S:14](Cl)(=[O:16])=[O:15])=[CH:9][CH:8]=1>C1COCC1>[CH2:1]([NH:5][S:14]([CH2:13][C:10]1[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=1)(=[O:15])=[O:16])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 227304(4-Chlorophenyl)methanesulfonyl chloride

Product 1

HCID 18891362N-butyl-1-(4-chlorophenyl)methanesulfonamideYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butylamine (3.25 g, 44.43 mmol) was dissolved in THF (25 mL) and it was then cooled in an ice-bath. ((4-Chlorophenyl)methyl)sulfonyl chloride (5.0 g, 22.21 mmol) in THF (25 mL) was dropped in. The cooling-bath was removed after the addition. The mixture was stirred for 2 h and then evaporated to dryness. DCM (50 mL) was added to the residue. It was washed with HCl (5%, 10 mL), water (30 mL×3) and brine (20 mL), dried (MgSO4) and evaporated to give the title compound (5.43 g, 93%) as a solid; 1H NMR (400 MHz, CDCl3): δ 7.36 (d, 2H), 7.32 (d, 2H), 4.19 (s, 2H), 4.11 (bt, 1H), 2.99 (dd, 2H), 1.50-1.43 (m, 2H), 1.36-1.26 (m, 2H), 0.90 (t, 3H); Mass Spectrum: M−H+ 260.

Workup

  1. temperatureit was then 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 washed with HCl (5%, 10 mL), water (30 mL×3) and brine (20 mL)
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-47625a4f4d8f4d60b938103a341d55db
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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