Water → 6-(3-(Hydroxymethyl)phenylthio)nicotinonitrile

HRID 2266997Notes

Reaction equation

HRID 2266997 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([S:9][C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13](O)=[O:14])=[N:7][CH:8]=1)#[N:2].[BH4-].[Na+].O>S(Cl)(Cl)=O.O1CCOCC1>[OH:14][CH2:13][C:12]1[CH:11]=[C:10]([S:9][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 641647833-(5-Cyano-pyridin-2-ylsulfanyl)-benzoic acid

Product 1

HCID 685330886-(3-(Hydroxymethyl)phenylthio)nicotinonitrileYield 57%

Reagents, catalysts & solvents 2

HCID 24386Thionyl ChlorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 3-(5-cyano-pyridin-2-ylsulfanyl)-benzoic acid (1.25 g, 4.88 mmol) in thionyl chloride (50 mL) and stir. Heat to reflux. After 2 hours, concentrate under reduced pressure to give a residue. Dissolve residue in dioxane (100 mL) and add sodium borohydride (1.85 g, 48.8 mmol). Heat to 50° C. After 2 hours, cool to ambient temperature and add water. Extract with ethyl acetate, combine organic layers, dry with sodium sulfate, filter and concentrate to give the title compound as a yellow oil (670 mg, 57%): 1H NMR (DMSO-d6) δ 4.56 (d, 2H), 5.33 (t, 1H), 7.06 (d, 1H), 7.49 (m, 3H), 7.57 (m, 1H), 8.08 (dd, 1H), 8.82 (dd, 1H).

Workup

  1. temperatureHeat to reflux
  2. concentrationconcentrate under reduced pressure
  3. customto give a residue
  4. waitAfter 2 hours
  5. temperaturecool to ambient temperature
  6. extractionExtract with ethyl acetate
  7. dry with materialdry with sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-b9d40c31847040f19fbc0219af5395aa
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

Loading…