Triethylamine → HCID 58764251, compound

HRID 2387028Notes

Reaction equation

HRID 2387028 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:11])([CH3:10])[CH3:9])=[C:4]([F:12])[CH:3]=1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl.Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][S:21]([CH3:20])(=[O:23])=[O:22])([CH3:10])[CH3:9])=[C:4]([F:12])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 587641802460749-55-5

Product 1

HCID 58764251HCID 58764251, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To 1-(4-bromo-2-fluoro-phenyl)-1-methyl-ethylamine (1.2 g, 5.4 mmol) and triethylamine (900 μL, 6.5 mmol) in dichloromethane (10 mL) at room temperature was added methanesulfonyl chloride (500 μL, 6.5 mmol). The solution was stirred 16 h, diluted in 1N HCl(aq) 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. Flash chromatography (SiO2, 40% ethyl acetate/hexane) gave a white solid (950 mg, 57%). 1H NMR (300 MHz, CDCl3): δ ppm 1.76 (s, 6 H) 2.74 (s, 3 H) 4.88 (s, 1 H) 7.24 (d, J=1.51 Hz, 1 H) 7.27-7.30 (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

Sources & evidence

ORD record
ord-5fa1d4972c0a4dc9866ef1ec0410a800
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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