Ammonia → Cyclopentaneethanesulfonamide

HRID 433894Notes

Reaction equation

HRID 433894 reaction equation
[CH:1]1([CH2:6][CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:12]>O1CCCC1>[CH:1]1([CH2:6][CH2:7][S:8]([NH2:12])(=[O:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 18756079405219-36-5

Product 1

HCID 205368Cyclopentaneethanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(cyclopentyl)ethanesulfonyl chloride (14.1 g, 71.4 mmol) in dry tetrahydrofuran (40 ml) was saturated with gaseous ammonia at 0° C. The resulting solution was stirred at room temperature under nitrogen for 2 hours and then concentrated under vacuum. The residue was dissolved in ethyl acetate (50 ml) and water (50 ml) and the aqueous phase was then acidified to pH 2 with 2.0 M aqueous hydrochloric acid. The organic phase was separated and then washed with water (2×30 ml), dried (sodium sulfate) and concentrated under vacuum. Purification of the residue by chromatography on silica (500 g) using 65/35 pentane/ethyl acetate as eluant gave the title compound as an off-white solid (6.48 g), Rf 0.7 (pentane/ethyl acetate 1:1).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  3. customThe organic phase was separated
  4. washwashed with water (2×30 ml)
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated under vacuum
  7. customPurification of the residue by chromatography on silica (500 g)

Sources & evidence

ORD record
ord-a8b11f69b493469bb0b42e597cf844bd
Source dataset
uspto-grants-2003_12
Patent number
US06670362B2

Reaction notes

Loading…