Hydroxyamine hydrochloride → HCID 9906336, compound

HRID 1856826Notes

Reaction equation

HRID 1856826 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:19][C:6]2=[C:7]([C:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:13])[S:8][C:9]([S:10][CH3:11])=[C:5]2[C:4](=[O:20])[C:3]1=[CH:21]O.Cl.[NH2:25]O>CCO.O>[CH3:1][C:2]1([CH3:23])[C:3]2[CH:21]=[N:25][O:20][C:4]=2[C:5]2=[C:9]([S:10][CH3:11])[S:8][C:7]([C:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:13])=[C:6]2[CH2:19]1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 70093552HCID 70093552, compound

Product 1

HCID 9906336HCID 9906336, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6,6-dimethyl-5-hydroxymethylene-3-methylthio-1-(pyrrolidin-1-ylcarbonyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (173 mg, 0.49 mmol) in EtOH (4 mL) and water (0.7 mL) was added hydroxylamine hydrochloride (38 mg, 0.54 mmol). The solution was heated at reflux for 2 h then cooled to room temperature and the solvent evaporated. The residue was partitioned between EtOAc (20 mL) and water (20 mL), the organic layer separated, dried (Na2SO4) and evaporated. The residue was triturated with hexane/Et2O and the resultant yellow solid (131 mg, 77%) collected by filtration. mp 114-116° C. C17H2ON20N2S2O2.0.1(H2O) requires: C, 58.29; H, 5.81; N, 8.00%. Found: C, 58.05; H, 5.59; N, 7.65%. 1H NMR (360 MHz, CDCl3) δ1.26 (6H, s), 1.94-1.98 (4H, m), 2.63 (3H, s), 2.90 (2H, s), 3.56-3.67 (4H, m), 8.20 (1H, s). MS (ES+) 349 (M+1).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2 h
  3. customthe solvent evaporated
  4. customThe residue was partitioned between EtOAc (20 mL) and water (20 mL)
  5. customthe organic layer separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was triturated with hexane/Et2O
  9. filtrationthe resultant yellow solid (131 mg, 77%) collected by filtration

Sources & evidence

ORD record
ord-a9db84e84b82476e930ab89cd0503002
Source dataset
uspto-grants-2000_11
Patent number
US06143773

Reaction notes

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