Water → HCID 68535053, compound

HRID 2266995Notes

Reaction equation

HRID 2266995 reaction equation
[C:1]([C:3]1[C:4]([S:9][C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13](O)=[O:14])=[N:5][CH:6]=[CH: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:4]2[N:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]#[N:2])[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 64166355HCID 64166355, compound

Product 1

HCID 68535053HCID 68535053, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 24386Thionyl ChlorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 3-(3-cyano-pyridin-2-ylsulfanyl)-benzoic acid (1.50 g, 5.85 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 μL) and add sodium borohydride (2.21 g, 58.5 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 (1.20 g, 85%): 1H NMR (DMSO-d6) δ 4.54 (d, 2H), 5.30 (t, 1H), 7.37 (dd, 1H), 7.43 (m, 3H), 7.50 (m, 1H), 8.29 (dd, 1H), 8.56 (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-913cc3e5b9604c1887e2d4e653ec7dee
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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