Potassium Carbonate → 4,5-Dimethylthiazole-2-carbaldehyde oxime

HRID 530818Notes

Reaction equation

HRID 530818 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH:8]=O)[S:5][C:6]=1[CH3:7].Cl.[NH2:11][OH:12].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CCOC(C)=O>[CH3:1][C:2]1[N:3]=[C:4]([CH:8]=[N:11][OH:12])[S:5][C:6]=1[CH3:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 145989794,5-Dimethyl-1,3-thiazole-2-carbaldehyde

Product 1

HCID 1366442314,5-Dimethylthiazole-2-carbaldehyde oxime

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4,5-dimethylthiazole-2-carbaldehyde (987 mg, 7.0 mmol) in 1,4-dioxane (35 mL) was added hydroxylamine hydrochloride (1.45 g, 21 mmol) and K2CO3 (3.8 g, 28 mmol). The resulting mixture was stirred at 100° C. for 2 hours and then diluted with EtOAc (150 mL), washed with H2O (30 mL*2). The organic layer was dried over Na2SO4, filtered and concentrated to give the crude product which was used for next step without further purification. LCMS m/z (M+H) 157.1 found, 157.1 required.

Workup

  1. washwashed with H2O (30 mL*2)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7d75e8b041a74f988bb0ee099c2ef2b0
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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