Butylamine → N-butyl-1-(3-chlorophenyl)methanesulfonamide

HRID 729249Notes

Reaction equation

HRID 729249 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH2:13]([NH2:17])[CH2:14][CH2:15][CH3:16]>C1COCC1>[CH2:13]([NH:17][S:9]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)(=[O:11])=[O:10])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 2757802(3-Chlorophenyl)methanesulfonyl chloride

Product 1

HCID 68661517N-butyl-1-(3-chlorophenyl)methanesulfonamideYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (3-chlorophenyl)methanesulfonyl chloride (3.00 g, 13.33 mmol) in dry THF (50 mL) was added dropwise to a solution of butylamine (2.63 mL, 26.65 mmol) in dry THF (50 mL) at 0° C. and under an atmosphere of nitrogen. After the addition was completed the ice-bath was removed and the mixture was stirred at rt for 1.5 h. It was evaporated and the residue was partitioned between DCM and HCl (1M). The combined organic layers were washed with water, dried with MgSO4 and evaporated to dryness to give the title compound (2.89 g, 83%) as a white powder; 1H NMR (500 MHz, CDCl3): δ 7.29-7.42 (m, 4H), 4.22 (s, 2H), 4.16 (bs, 1H), 2.99-3.05 (m, 2H), 1.46-1.53 (m, 2H), 1.29-1.38 (m, 2H), 0.92 (t, 3H); 13C NMR (125 MHz, CDCl3): δ 132.2, 129.0, 128.3, 127.7, 126.6, 126.4, 55.9, 41.2, 30.0, 17.3, 11.21; Mass Spectrum: M−H+ 260.

Workup

  1. additionAfter the addition
  2. customwas removed
  3. customIt was evaporated
  4. customthe residue was partitioned between DCM and HCl (1M)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried with MgSO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d68d0c40adf740aaad60862dcac4fd25
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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