Triethylamine → HCID 58764251, compound

HRID 859639Notes

Reaction equation

HRID 859639 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-772b0ac519674b738b49f71672cb7eb8
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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