Hydroxyamine hydrochloride → HCID 21184557, compound

HRID 1385300Notes

Reaction equation

HRID 1385300 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:17][C:6]2=[C:7]([C:12](=[O:16])[CH:13]=[CH:14]O)[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:18])[CH2:3]1.Cl.[NH2:21]O>C(O)C.O>[CH3:1][C:2]1([CH3:19])[CH2:17][C:6]2=[C:7]([C:12]3[O:16][N:21]=[CH:14][CH:13]=3)[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:18])[CH2:3]1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 70099319HCID 70099319, compound

Product 1

HCID 21184557HCID 21184557, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 6,6-dimethyl-1-(3-hydroxy-1-oxoprop-2-enyl)-3-methylthio-4,5,6,7-tetrahydrobenzo [c]thiophen-4-one (200 mg, 0.68 mmol) in ethanol (14 mL) and water (1.6 mL) was heated to 80° C., after which hydroxylamine hydrochloride (52 mg, 0.74 mmol) was added. The mixture was heated at reflux for 4 h, after which time the solvent was removed in vacuo and the residue triturated in hexane/ether. The isoxazole (50 mg, 20%) was isolated as a colourless solid. mp 143-145° C. 1H NMR (360 MHz, CDCl3) δ 1.09 (6H, s), 2.45 (2H, s), 2.64 (3H, s), 2.90 (2H, s), 6.28 (1H, d, J=1.9 Hz), 8.29 (1H, d, J=1.9 Hz). MS (ES+) 294 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 h
  3. customafter which time the solvent was removed in vacuo
  4. customthe residue triturated in hexane/ether

Sources & evidence

ORD record
ord-cb3eaf54f0c542ebaa6ea72237b70654
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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