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

HRID 2387079Notes

Reaction equation

HRID 2387079 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, 3 H) 2.69 (q, J=7.54 Hz, 2 H) 2.90 (s, 3 H) 4.27-4.31 (m, 2H) 4.40-4.50 (m, 1 H) 7.21 (d, J=8.10 Hz, 1 H) 7.32-7.40 (m, 2 H).

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-a259e1833e344773ad0dd2dc74ba2b4c
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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