Water → 2-(Morpholin-4-yl)-1,3-thiazole-5-carbaldehyde

HRID 1186375

Reaction equation

HRID 1186375 reaction equation
Cl[C:2]1[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=1.C(=O)([O-])[O-].[K+].[K+].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.O>C(#N)C.C(OCC)(=O)C>[O:18]1[CH2:19][CH2:20][N:15]([C:2]2[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=2)[CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 14797652-Chloro-1,3-thiazole-5-carbaldehyde

Product 1

HCID 14797702-(Morpholin-4-yl)-1,3-thiazole-5-carbaldehydeYield 66.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chlorothiazole-5-carbaldehyde (200 mg, 1.36 mmol) was dissolved in acetonitrile (4 mL). To this, potassium carbonate (376 mg, 2.72 mmol) and morpholine (0.237 mL, 2.72 mmol) were added at room temperature and the mixture was stirred at the same temperature for 23.5 hours. After water was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=15/1) to give 2-morpholinothiazole-5-carbaldehyde (179 mg, yield: 66%).

Workup

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-b45d16598c424fb1b190567e53e95327
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Linked notes

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