Ethanol → HCID 76545642, compound

HRID 898804Notes

Reaction equation

HRID 898804 reaction equation
O=[C:2]([C:8]1[S:12][CH:11]=[N:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(O)C.C([O-])(=O)C.[Na+].Cl.[NH2:22][OH:23]>CCCCCC.C(OCC)(=O)C>[OH:23][N:22]=[C:2]([C:8]1[S:12][CH:11]=[N:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 18922168HCID 18922168, compound

Product 1

HCID 76545642HCID 76545642, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
85 °C

Procedure

To a r.b. flask (500 cm3) was added the ethyl oxo-thiazol-5-ylacetate (6.30 g, 34.02 mmol) to ethanol (ca. 180 cm3) with stirring. Sodium acetate (3.06 g, 37.30 mmol) and hydroxylamine hydrochloride (3.78 g, 54.43 mmol) were then added to give an off-white suspension. This was brought to reflux at 85° C. for 1 hour. Reaction monitored by TLC (60% hexane/ethyl acetate; s.m. r.f 0.5, prod. r.f. 0.3.). Reaction cooled and concentrated in vacuo. Product taken up in ethyl acetate (c.a. 200 cm3) and washed with 5% hydrochloric acid solution. Ethyl acetate layer was dried over magnesium sulphate and evaporated to dryness to give a cream solid (6.372 g, 31.825 mmol) [94% Yield].

Workup

  1. customto give an off-white suspension
  2. customReaction
  3. customReaction
  4. temperaturecooled
  5. concentrationconcentrated in vacuo
  6. washwashed with 5% hydrochloric acid solution
  7. dry with materialEthyl acetate layer was dried over magnesium sulphate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-37a7a060784c4cd593ecb175f8a3c439
Source dataset
uspto-grants-2008_04
Patent number
US07351822B2

Reaction notes

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