Hydroxyamine hydrochloride → HCID 74003791, compound

HRID 1377775Notes

Reaction equation

HRID 1377775 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH2:18][CH2:17][C:16](=O)[CH:15]=3)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22]>CCO.N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH2:18][CH2:17][C:16](=[N:21][OH:22])[CH:15]=3)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 22915421HCID 22915421, compound

Product 1

HCID 74003791HCID 74003791, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21975839Pyridine ethanolSolvent

Procedure

To a stirred solution of 3-[5-(4-fluorophenylthio)-2-furyl]-2-cyclopentenone (5.9 g; 21.5 mM) in EtOH-pyridine (50 ml-12 ml) was added hydroxylamine hydrochloride (2.24 g; 32.3 mM) at room temperature. After stirring overnight, solvent was removed. To the residue was added 0.5N aqueous HCl (80 ml), and the whole was extracted with ethyl acetate (100 ml×2). The combined organic layer was washed with water (70 ml), brine (70 ml), dried over MgSO4, and concentrated in vacuo to give 6 g (yield 97%) of crude subtitle compound as a brown oil, which was used without further purification.

Workup

  1. customsolvent was removed
  2. additionTo the residue was added 0.5N aqueous HCl (80 ml)
  3. extractionthe whole was extracted with ethyl acetate (100 ml×2)
  4. washThe combined organic layer was washed with water (70 ml), brine (70 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b75f7613f49540e8887f77c97c6e2e2c
Source dataset
uspto-grants-1997_09
Patent number
US05665768

Reaction notes

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