Ammonia → 405219-37-6

HRID 433893Notes

Reaction equation

HRID 433893 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10](Cl)(=[O:12])=[O:11])=[CH:4][CH:3]=1.[NH3:14].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10]([NH2:14])(=[O:12])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 311Citric AcidHCID 27590982-(4-Fluoro-phenyl)-ethanesulfonyl chloride

Product 1

HCID 18756082405219-37-6

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-(4-flourophenyl)ethanesulfonyl chloride (0.7 g, 3.3 mmol) and concentrated aqueous ammonia (0.88 specific gravity, 10 ml) in ethanol (5 ml) was stirred at room temperature overnight. The reaction mixture was diluted with water (10 ml), acidified to pH 4 with citric acid (1.0 M) and then extracted with dichloromethane. The organic extracts were dried by filtering through an organic-only, permeable membrane and then concentrated under vacuum. The residue was purified by chromatography on a Biotage® Flash 40 (s) column (40 g silica) using 10-20% ethyl acetate/dichloromethane as eluant to give the title compound as an off white solid, (0.66 g).

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic extracts were dried
  3. filtrationby filtering through an organic-only, permeable membrane
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by chromatography on a Biotage® Flash 40 (s) column (40 g silica)

Sources & evidence

ORD record
ord-93b2c4ebd40947d599a7ee81c3f486f1
Source dataset
uspto-grants-2003_12
Patent number
US06670362B2

Reaction notes

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