Water → 2-(2,4-Dimethoxy-benzyl)-5-(5-{1-[hydroxyimino]-4-methylpentyl}-thiophen-2-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 1592005Notes

Reaction equation

HRID 1592005 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][N:8]([CH2:12][C:13]2[S:14][C:15]([C:18](=O)[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:16][CH:17]=2)[S:7]1(=[O:26])=[O:25].[OH2:33].Cl.[NH2:35]O>CCO>[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][N:8]([CH2:12][C:13]2[S:14][C:15]([C:18](=[N:35][OH:33])[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:16][CH:17]=2)[S:7]1(=[O:25])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 67138236HCID 67138236, compound

Product 1

HCID 865910402-(2,4-Dimethoxy-benzyl)-5-(5-{1-[hydroxyimino]-4-methylpentyl}-thiophen-2-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title D compound, 2-(2,4-dimethoxy-benzyl)-5-[5-(4-methyl-pentanoyl)-thiophen-2-ylmethyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (50 mg, 0.10 mmol) is dissolved in EtOH (5 mL) and water (1 mL) is added. Hydroxylamine hydrochloride (72 mg, 1.0 mmol) is added and the mixture is heated at reflux for 4 h. The solvent is evaporated and the residue is partitioned between EtOAc and water. The organic layer is dried over anhydrous MgSO4 and concentrated to dryness to afford 2-(2,4-dimethoxy-benzyl)-5-(5-(1-[-hydroxyimino]-4-methyl-pentyl)-thiophen-2-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a clear oil: [M+1]+=496.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 4 h
  3. customThe solvent is evaporated
  4. customthe residue is partitioned between EtOAc and water
  5. dry with materialThe organic layer is dried over anhydrous MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-88eb302cca7545a4aa8c22031d3d60ca
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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