Dimethyl Sulfoxide → HCID 57626401, compound

HRID 1693687Notes

Reaction equation

HRID 1693687 reaction equation
Br[C@@H:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH2:3]C.[C-:13]#[N:14].[K+].[CH3:16]S(C)=O>>[F:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][C@H:2]([CH3:3])[CH2:16][C:13]#[N:14])=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 9032Potassium Cyanide2×HCID 67278503HCID 67278503, compound

Product 1

HCID 57626401HCID 57626401, compoundYield 54.6%

Procedure

To a stirred solution of the bromide 5 (12.82 g, 55 mmol) dissolved in DMSO (60 mL) was added dry KCN (1.95 g, 30 mmol), and the reaction mixture was stirred at 40° C. for 3.5 hours until the KCN powder had disappeared. The reaction was quenched with saturated aqueous NH4Cl solution (150 mL). After extraction with ethyl acetate, the combined organic layers were washed with 1N NaOH, water, and brine. After drying over Na2SO4, the organic layer was filtered and ethyl acetate was evaporated in vacuo. The residue was then vacuum distilled at 130-135° C. at 1.0 mm Hg to give 5.35 g (54.6%) of product as a colorless oil. Further distillation yielded 5.8 g (45.2%) of recovered bromide 5. 1H NMR (CDCl3) δ 7.01-6.98 (m, 2H), 6.90-6.87 (m, 2H), 4.55-4.52 (m, 1H), 2.68 (d, J=5.5 Hz, 2H), 1.48 (d, J=6.5 Hz, 3H). EI-MS (m/z) 179 (M++1). The reaction is shown as follows.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl solution (150 mL)
  2. extractionAfter extraction with ethyl acetate
  3. washthe combined organic layers were washed with 1N NaOH, water, and brine
  4. dry with materialAfter drying over Na2SO4
  5. filtrationthe organic layer was filtered
  6. customethyl acetate was evaporated in vacuo
  7. distillationvacuum distilled at 130-135° C. at 1.0 mm Hg

Sources & evidence

ORD record
ord-96f1e89f9de84596be07c46978334b9d
Source dataset
uspto-grants-2012_04
Patent number
US08158667B2

Reaction notes

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