Hydroxyamine hydrochloride → 5-(Thiophen-2-YL)-1,2-oxazole

HRID 2184794Notes

Reaction equation

HRID 2184794 reaction equation
CN(C)[C:3](=[CH2:11])[C:4]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)=[O:5].Cl.[NH2:14]O>CO>[S:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[C:4]1[O:5][N:14]=[CH:11][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 22288452beta-Dimethylamino-1-(2-thienyl)-2-propen-1-one

Product 1

HCID 120499865-(Thiophen-2-YL)-1,2-oxazoleYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of β-dimethylamino-1-(2-thienyl)-2-propen-1-one (1) (18.1 g, 100 mmol) and hydroxylamine hydrochloride (7.0 g, 101 mmol) in anhydrous methanol (100 mL) is refluxed under nitrogen for 2 hrs. The reaction mixture is cooled, concentrated and partitioned between water and dichloromethane. The dichloromethane layer is dried with anhydrous sodium sulfate, filtered and concentrated to yield product (2) as a dark yellow-orange oil (14.7 g, 97 mmol, 97%).

Workup

  1. temperatureis refluxed under nitrogen for 2 hrs
  2. temperatureThe reaction mixture is cooled
  3. concentrationconcentrated
  4. custompartitioned between water and dichloromethane
  5. dry with materialThe dichloromethane layer is dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-336c0b89ef8d4754915d17a80ed200fe
Source dataset
uspto-grants-2002_06
Patent number
US06399621B1

Reaction notes

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