Dimethyl Sulfoxide → HCID 81645951, compound

HRID 2278226Notes

Reaction equation

HRID 2278226 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[N:14]1([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 5229404-Fluoro-2-(trifluoromethyl)benzaldehyde

Product 1

HCID 81645951HCID 81645951, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 100 mL round-bottom flask was charged with 4-fluoro-2-(trifluoromethyl)benzaldehyde (1.00 g, 5.21 mmol, 1.00 equiv), morpholine (0.500 g, 5.74 mmol, 1.10 equiv), potassium carbonate (1.40 g, 10.1 mmol, 2.00 equiv), DMSO (15 mL). The resulting solution was stirred overnight at 100° C., diluted with H2O (10 mL), extracted with ethyl acetate (3×10 mL). The organic layers were combined and washed with brine (1×50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (25/75) to provide 1.00 g (74% yield) of 4-(morpholin-4-yl)-2-(trifluoromethyl)benzaldehyde as a yellow solid. LCMS (ESI, m/z): 260 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washwashed with brine (1×50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (25/75)

Sources & evidence

ORD record
ord-e1b6491f53ed46ff9e6ad3a9b777b710
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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