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

HRID 1934796Notes

Reaction equation

HRID 1934796 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 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Compound 3 (18.1g, 100 mmol) and hydroxylamine hydrochloride (7.0 g, 101 mmol) in 100 mL of anhydrous methanol was refluxed under nitrogen for 2 hours. The reaction mixture was cooled, concentrated and partitioned between water and dichloromethane. The dichloromethane layer was dried with anhydrous sodium sulfate, filtered and concentrated to yield compound 4 as a dark yellow-orange oil (14.1 g, 93.3 mmol, 93%). GC/MS, m/z=151 at tR=8.30 min (100%). LC/MS, [M+H]=152.

Workup

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

Sources & evidence

ORD record
ord-61c270230fe54335aecd3df8e825941c
Source dataset
uspto-grants-2002_05
Patent number
US06384221B1

Reaction notes

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