O-(5-Chloro-thiophen-2-ylmethyl)-hydroxylamine → HCID 53817257, compound

HRID 1761802Notes

Reaction equation

HRID 1761802 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][O:8][NH2:9])=[CH:4][CH:3]=1.[C:10]([C:13]1[C:14](=[O:29])[CH2:15][CH:16]([CH:23]2[CH2:28][CH2:27][CH2:26][S:25][CH2:24]2)[CH2:17][C:18]=1[O:19][C:20](=[O:22])[CH3:21])(=O)[CH3:11]>C(O)C>[C:20]([O:19][C:18]1[CH2:17][CH:16]([CH:23]2[CH2:28][CH2:27][CH2:26][S:25][CH2:24]2)[CH2:15][C:14](=[O:29])[C:13]=1[C:10](=[N:9][O:8][CH2:7][C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:11])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 10986580O-(5-Chloro-thiophen-2-ylmethyl)-hydroxylamineHCID 20043437HCID 20043437, compound

Product 1

HCID 53817257HCID 53817257, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.34 g (2.0 mmol) of (5-chlorothien-2-yl)methoxyamine is added to a stirred solution of 0.59 g (2.0 mmol) of 2-acetyl-3-acetyloxy-5-(tetrahydro-2H-thiopyran-3-yl)cyclohex-2-en-1-one in 10 ml of absolute ethanol. After stirring overnight at room temperature, the reaction mixture is concentrated under reduced pressure. The resulting residue is diluted with 25 ml of dichloromethane and washed twice with 10 ml of saturated sodium chloride solution. The washed extract is then dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The product can then be purified by column chromatography employing tetrahydrofuran-hexane (1:2 by volume) as eluent to afford the title compound.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. additionThe resulting residue is diluted with 25 ml of dichloromethane
  3. washwashed twice with 10 ml of saturated sodium chloride solution
  4. extractionThe washed extract
  5. dry with materialis then dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe product can then be purified by column chromatography

Sources & evidence

ORD record
ord-d695c61ca3364c839606a59da6e2bea9
Source dataset
uspto-grants-1989_05
Patent number
US04828601

Reaction notes

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