Triethylamine → N-(4-Bromo-2-ethyl-benzyl)-methanesulfonamide

HRID 1438272Notes

Reaction equation

HRID 1438272 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([CH2:10][CH3:11])[CH:3]=1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][S:20]([CH3:19])(=[O:22])=[O:21])=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58764124(4-Bromo-2-ethylphenyl)methanamine

Product 1

HCID 58764228N-(4-Bromo-2-ethyl-benzyl)-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 4-bromo-2-ethyl-benzylamine (650 mg, 3 mmol) and triethylamine (500 μL, 3.6 mmol) in dichloromethane (5 mL) at room temperature was added methanesulfonyl chloride (283 μL, 3.6 mmol). The solution was stirred 1 h, diluted in water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and concentrated in vacuo to an off-white solid (880 mg, 100%). 1H NMR (300 MHz, CDCl3): δ ppm 1.25 (t, J=7.54 Hz, 3H) 2.69 (q, J=7.54 Hz, 2H) 2.90 (s, 3H) 4.27-4.31 (m, 2H) 4.40-4.50 (m, 1H) 7.21 (d, J=8.10 Hz, 1H) 7.32-7.40 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium bicarbonate
  3. dry with materialsaturated sodium chloride, dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to an off-white solid (880 mg, 100%)

Sources & evidence

ORD record
ord-1a074418629c460fa60d0f7d203a0ff4
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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