Triethylamine → HCID 59598232, compound

HRID 2266032Notes

Reaction equation

HRID 2266032 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[F:12].CCN(CC)CC.[CH3:20][S:21](Cl)(=[O:23])=[O:22].[OH-].[Na+]>C(Cl)Cl.CCOC(C)=O.Cl.C1COCC1.CO>[C:9]([C:5]1[CH:4]=[C:3]([F:12])[C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])=[C:7]([F:8])[CH:6]=1)(=[O:11])[CH3:10]

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 211143061-(4-Amino-3,5-difluorophenyl)ethan-1-one

Product 1

HCID 59598232HCID 59598232, compoundYield 317.2%

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1-(4-amino-3,5-difluoro-phenyl)-ethanone (2.35 g, 13.73 mmol) and Et3N (2 mL) in CH2Cl2 (10 mL) was added dropwise MsCl (2.34 mL, 2.34 mmol) at 0° C. The mixture was stirred for 3 hours at room temperature. The mixture was then diluted with EtOAc and 1N-HCl. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was used directly in the following reaction. The crude residue was dissolved in THF (8 mL), after then was added 1N NaOH (4 mL) and CH3OH (4 mL) to the solution. After stirred for 5 hrs at room temperature, the mixture was diluted with EtOAc and 1N-HCl. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by chromatography to afford N-(4-acetyl-2,6-difluoro-phenyl)-methanesulfonamide (1.85 g, 54%).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was used directly in the following reaction
  6. stirringAfter stirred for 5 hrs at room temperature
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude residue was purified by chromatography

Sources & evidence

ORD record
ord-a5f3a660cdc049cca209a73d048d5cdd
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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