Methylamine → HCID 21069935, compound

HRID 348129Notes

Reaction equation

HRID 348129 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][NH2:14]>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([S:8]([NH:14][CH3:13])(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 1362865-Fluoro-2-methylbenzenesulphonyl chloride

Product 1

HCID 21069935HCID 21069935, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-fluoro-2-methyl-benzenesulfonyl chloride (4.18 g, 20 mmol) in acetone (20 mL) was added a 40% aqueous solution of methylamine (4.5 mL, 60 mmol) under nitrogen and the mixture stirred for 5 min. Acetone was removed in vacuo and the aqueous residue extracted with CH2Cl2. The CH2Cl2 extract was dried (Na2SO4), filtered, concentrated and the residue purified by column chromatography (SiO2, 10% ether in CH2Cl2) to provide 3.9 g (19.2 mmol, Yield 96%) of the title compound as a white solid; 1H NMR (500 MHz, CDCl3) δ ppm: 2.59 (3H, s), 2.67 (3H, d, J=5.5 Hz), 4.41 (1H, brs), 7.13–7.20 (1H, m), 7.29 (1H, dd, J=8.2, 5.5 Hz), 7.69 (1H, J=8.6, 2.1 Hz); LC/MS m/z 204 (M+H).

Workup

  1. customAcetone was removed in vacuo
  2. extractionthe aqueous residue extracted with CH2Cl2
  3. extractionThe CH2Cl2 extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue purified by column chromatography (SiO2, 10% ether in CH2Cl2)

Sources & evidence

ORD record
ord-203822cb835e4bbfa21398de4802239f
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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