Triethylamine → N-(5-bromo-2,4-bis(2,4-difluorophenoxy)phenyl)methanesulfonamide

HRID 633527Notes

Reaction equation

HRID 633527 reaction equation
[Br:1][C:2]1[C:3]([O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])=[C:6]([CH:8]=1)[NH2:7].C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[Br:1][C:2]1[C:3]([O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])=[C:6]([NH:7][S:35]([CH3:34])(=[O:37])=[O:36])[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 904177805-Bromo-2,4-bis(2,4-difluorophenoxy)aniline

Product 1

HCID 90416323N-(5-bromo-2,4-bis(2,4-difluorophenoxy)phenyl)methanesulfonamideYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the product from Example 13B (0.52 g, 1.214 mmol) and triethylamine (0.423 mL, 3.04 mmol) in dichloromethane (12.14 mL) was added dropwise methanesulfonyl chloride (0.207 mL, 2.67 mmol). The mixture was stirred for 2 hours at ambient temperature, and concentrated. The residue was dissolved in a mixture of dioxane (4 mL) and 1 M sodium hydroxide (1 mL) and heated for 1 hour at 90° C. The mixture was cooled and diluted with ethyl acetate, brought to pH 7 with 1 M HCl and the organic layer was separated, dried (anhydrous Na2SO4), filtered, and concentrated. Purification by chromatography (silica gel, 20-60% ethyl acetate in heptanes) afforded the title compound (0.5 g, 81%).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in a mixture of dioxane (4 mL) and 1 M sodium hydroxide (1 mL)
  3. temperatureheated for 1 hour at 90° C
  4. temperatureThe mixture was cooled
  5. additiondiluted with ethyl acetate
  6. customthe organic layer was separated
  7. dry with materialdried (anhydrous Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by chromatography (silica gel, 20-60% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-bd8e4fe1834b4f06a624c44e7f47137e
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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