Dimethyl Sulfoxide → HCID 17985402, compound

HRID 910110Notes

Reaction equation

HRID 910110 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([CH2:11][C:12](OC)=O)=[CH:4][NH:3]1.[C-]#[N:17].[Na+].CS(C)=O>C(OCC)(=O)C>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([CH2:11][C:12]#[N:17])=[CH:4][NH:3]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 86597618HCID 86597618, compound

Product 1

HCID 17985402HCID 17985402, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine methyl (4-oxo-4,5-dihydrofuro[3,2-c]pyridin-7-yl)acetate (4.42 g, 21.3 mmol), sodium cyanide (5.22 g, 106 mmol), and dimethylsulfoxide (44 mL) and heat at 80° C. for 1 hour. Cool to room temperature, pour into ethyl acetate, wash sequentially with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride, dry over magnesium sulfate, filter, and concentrate under reduced pressure to provide the desired compound (3.63 g, 63%).

Workup

  1. washwash sequentially with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  2. dry with materialdry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-e2917aecc8c54e41bc149b9192428958
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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