Water → HCID 58133725, compound

HRID 336904Notes

Reaction equation

HRID 336904 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[S:15]([CH2:18][CH2:19][OH:20])(=[O:17])=[O:16].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>CC(C)=O.O>[OH:20][CH2:19][CH2:18][S:15]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:7]=1[CH:2]=[O:1])[C:11]#[N:12])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 58133844HCID 58133844, compound

Product 1

HCID 58133725HCID 58133725, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
160 °C

Procedure

In an Emrys microwave, 4-(1,3-dioxan-2-yl)-3-[(2-hydroxyethyl)sulfonyl]benzonitrile (1970 mg, 6.6 mmol) and pyridinium 4-toluenesulfonate (1249 mg, 4.97 mmol; 0.75 eq.) in acetone/water (1:1, 30 ml) were heated with stirring at 160° C. for 5 min. The reaction mixture was then added to water (200 ml) and extracted with ethyl acetate (8×50 ml). The combined organic phases were then washed with saturated sodium chloride solution (2×50 ml), dried over sodium sulfate, filtered and concentrated under reduced pressure. To increase the yield, the sodium chloride wash solution was reextracted with ethyl acetate. The title compound was obtained as a solid (1.57 g, 99% of theory).

Workup

  1. extractionextracted with ethyl acetate (8×50 ml)
  2. washThe combined organic phases were then washed with saturated sodium chloride solution (2×50 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. temperatureTo increase the yield
  7. washthe sodium chloride wash solution

Sources & evidence

ORD record
ord-d357cad37e8143b8b83eb6dd261cc3a3
Source dataset
uspto-grants-2014_11
Patent number
US08889700B2

Reaction notes

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