Dimethylamine → HCID 16753949, compound

HRID 1726563Notes

Reaction equation

HRID 1726563 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]>O1CCCC1>[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, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-fluoro-2-methyl-benzenesulfonyl chloride (4.18 g, 20 mmol) in tetrahydrofuran (25 mL) was added, dropwise, a solution of dimethylamine in tetrahydrofuran (2M, 25 mL, 50 mmol) over 15 min. and the mixture stirred for 5 min. The insoluble materials were filtered and the filtrate concentrated. The residue was purified by column chromatography (SiO2, 5% ether in CH2Cl2) to provide 4.3 g (Yield 90%) of the title compound as a clear oil: 1H NMR (500 MHz, CDCl3) δ ppm: 2.57 (3H, s) 2.82 (3H, s) 2.82 (3H, s) 7.12-7.18 (1H, m) 7.28 (1H, dd, J=8.2, 5.5 Hz) 7.59 (1H, dd, J=8.2, 2.1 Hz); LC/MC m/z 218 (M+H).

Workup

  1. filtrationThe insoluble materials were filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified by column chromatography (SiO2, 5% ether in CH2Cl2)

Sources & evidence

ORD record
ord-06368824e1164ae78f371bf438534572
Source dataset
uspto-grants-2009_02
Patent number
US07491819B1

Reaction notes

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