Hydroxyamine hydrochloride → 8-(1-Hydroxyiminoethyl)-10,11-dihydrodibenzo[b,f]thiepin-1,3-diol
Reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[C:15]([OH:19])[CH:16]=[C:17]([OH:18])[C:11]=3[CH2:10][CH2:9][C:8]=2[CH:20]=1)(=O)[CH3:2].Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>C(O)C.O>[OH:23][N:22]=[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[C:15]([OH:19])[CH:16]=[C:17]([OH:18])[C:11]=3[CH2:10][CH2:9][C:8]=2[CH:20]=1)[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
In ethanol, 180 mg of 8-acetyl-10,11-dihydrodibenzo[b,f]thiepin-1,3-diol (63) was dissolved, and an aqueous solution of 49 mg of hydroxylamine hydrochloride and 100 mg of sodium acetate dissolved in 1 mL of water was added thereto. The mixed solution was stirred at 120° C. for 3 hours, concentrated under reduced pressure and then, extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution and then, dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=1:1). Upon recrystallization from chloroform-hexane, 120 mg of skin-colored amorphous title compound was obtained (yield 63%).
Workup
- additionwas added
- concentrationconcentrated under reduced pressure
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materiala saturated sodium chloride solution and then, dried with anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=1:1)
- customUpon recrystallization from chloroform-hexane
Sources & evidence
- ORD record
- ord-7fa1a9e52b414036885191c69b488b3d
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06700013B2
Reaction notes
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