Hydroxyamine hydrochloride → 4H-Thieno[2,3-b]thiopyran-4-one, 5,6-dihydro-, oxime

HRID 1381692Notes

Reaction equation

HRID 1381692 reaction equation
[S:1]1[C:5]2[S:6][CH2:7][CH2:8][C:9](=O)[C:4]=2[CH:3]=[CH:2]1.Cl.[NH2:12][OH:13].O.C(O)C.C([O-])(=O)C.[Na+]>C(O)C>[N:12](=[C:9]1[CH2:8][CH2:7][S:6][C:5]2[S:1][CH:2]=[CH:3][C:4]1=2)[OH:13]

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 110302745,6-Dihydro-4H-thieno[2,3-b]thiopyran-4-oneHCID 19096565Water ethanol2×

Product 1

HCID 27397394H-Thieno[2,3-b]thiopyran-4-one, 5,6-dihydro-, oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5,6-dihydrothieno[2,3-b]thiopyran-4-one (5.0 g, 29.4 mmol) in ethanol (98 ml) was added a solution of hydroxylamine hydrochloride (4.9 g, 70.6 mmol) in 2:1 water-ethanol (27 ml). Sodium acetate.3H2O (9.6 g, 70.6 mmol) in 2:1 water-ethanol (27 ml) was added and the solution was heated at reflux for 2 hours. The reaction mixture was concentrated to dryness, water was added and the solid product (5.3 g, 98%) was collected and dried. An analytical sample was prepared by recrystallization from acetonitrile; m.p. 123°-124° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated to dryness, water
  4. additionwas added
  5. customthe solid product (5.3 g, 98%) was collected
  6. customdried
  7. customAn analytical sample was prepared by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-f1235213087641b2a64a573fc605cbde
Source dataset
uspto-grants-1989_02
Patent number
US04803286

Reaction notes

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