Water → 5-(4-tert-Butyl-cyclohexyloxy)-benzothiazole-2-carbaldehyde
Reaction equation
[Se](=O)=O.[O:4]1CCOCC1.O.[C:11]([CH:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:23]=[CH:24][C:25]3[S:29][C:28]([CH3:30])=[N:27][C:26]=3[CH:31]=2)[CH2:17][CH2:16]1)([CH3:14])([CH3:13])[CH3:12]>>[C:11]([CH:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:23]=[CH:24][C:25]3[S:29][C:28]([CH:30]=[O:4])=[N:27][C:26]=3[CH:31]=2)[CH2:17][CH2:16]1)([CH3:14])([CH3:13])[CH3:12]Participants
Conditions
- Temperature
- 65 °C
Procedure
Selenium dioxide (180 mg, 1.6 mmol) was combined with 1,4-Dioxane (5 mL, 60 mmol) and Water (0.5 mL, 30 mmol) at room, temperature open to the atmosphere. The mixture was then treated with 5-(4-tert-Butyl-cyclohexyloxy)-2-methyl-benzothiazole (250 mg, 0.82 mmol) and resulting mixture was heated to 65° C. for 2 hours. The heat was increased to 90° C. and 4 additional eq. of SeO2 were added. Reaction was stirred for additional 5 hours. LCMS shows nearly complete conversion. Reaction become dark and solids formed in reaction mixture. Reaction was cooled to RT and allowed to stand over night. Solids were removed via filtration. Concentrated to dryness then purified directly via column chromatography using a gradient of 0-40% Ethylacetate/hexane to give the title compound as a dark solid.
Workup
- customresulting mixture
- temperatureThe heat was increased to 90° C.
- addition4 additional eq. of SeO2 were added
- customReaction
- customReaction
- customsolids formed in reaction mixture
- customReaction
- temperaturewas cooled to RT
- waitto stand over night
- customSolids were removed via filtration
- concentrationConcentrated to dryness
- customthen purified directly via column chromatography
Sources & evidence
- ORD record
- ord-4f5ba1f39cc74608b9cdf6d708397e3b
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802659B2
Reaction notes
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