Dimethylamine → HCID 16753949, compound

HRID 897371Notes

Reaction equation

HRID 897371 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[CH3:13][NH:14][CH3:15]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([S:8]([N:14]([CH3:15])[CH3:13])(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 1362865-Fluoro-2-methylbenzenesulphonyl chloride

Product 1

HCID 16753949HCID 16753949, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-fluoro-2-methyl-benzenesulphonyl chloride (5.0 g, 24.0 mmol, Lancaster cat # 12627) dissolved in THF (100 mL) was saturated with dimethylamine gas and left to stir at room temperature for one hour. The ammonium chloride salts were then removed by vacuum filtration and the filtrate was concentrated to a yellow oil. The oil was dissolved in a minimal amount of ethyl acetate and purified on an Isco column (110 g silica) running a 10 to 25% EtOAc/Hexane gradient over 40 minutes. The collected fractions were concentrated in vacuo to afford the desired material as a yellow oil.

Workup

  1. waitleft
  2. customThe ammonium chloride salts were then removed by vacuum filtration
  3. concentrationthe filtrate was concentrated to a yellow oil
  4. dissolutionThe oil was dissolved in a minimal amount of ethyl acetate
  5. custompurified on an Isco column (110 g silica)
  6. customover 40 minutes
  7. concentrationThe collected fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-d8f06f850a2f4c2691e48f316a13761e
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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