Morpholine → HCID 59331549, compound

HRID 1881863Notes

Reaction equation

HRID 1881863 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10][CH3:11])[CH:5]=O.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C-:30]#[N:31].[K+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:30]#[N:31])[CH:7]=[CH:8][C:9]=1[S:10][CH3:11]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 9032Potassium CyanideHCID 521998p-Toluenesulfonic acid monohydrateHCID 18463640HCID 18463640, compound

Product 1

HCID 59331549HCID 59331549, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chloro-4-(methylsulfanyl)benzaldehyde (12.3 g) in tetrahydrofuran (50 mL) were added morpholine (13.4 mL), p-toluenesulfonic acid monohydrate (10.8 g) and a solution of potassium cyanide (4.50 g) in water (10 mL), and the mixture was heated under reflux for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and recrystallized from hexane-ethyl acetate to give the title compound (14.0 g, yield 95%) as colorless crystals.

Workup

  1. temperatureunder reflux for 16 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  7. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-a08af788a44a46d0861155e4c8d9c590
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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