4-Fluorobenzenesulfonyl chloride → HCID 3113419, compound

HRID 2084838Notes

Reaction equation

HRID 2084838 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][S:16]([C:13]1[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=1)(=[O:18])=[O:17])[CH3:3]

Participants

5

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 3113419HCID 3113419, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4.00 g (0.029 mol) of glycine ethyl ester hydrochloride in 40 mL of chloroform and 7.0 mL of pyridine was added 5.58 g (0.029 mol) of 4-fluorobenzenesulfonyl chloride and the reaction was stirred at room temperature for 15 h. The reaction mixture was then washed with water and 5% HCl solution and the organics were dried over MgSO4, filtered and concentrated in vacuo. The resulting white solid was washed with ether/hexanes (1:1) and dried in vacuo to provide 4.72 g (63%) of the sulfonamide as a white solid. Electrospray Mass Spec 261.8 (M+H)+.

Workup

  1. washThe reaction mixture was then washed with water and 5% HCl solution
  2. dry with materialthe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe resulting white solid was washed with ether/hexanes (1:1)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-320d7fb53e4d450399ee442432572554
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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