Dimethylformamide → HCID 57988764, compound

HRID 889042Notes

Reaction equation

HRID 889042 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:5][CH:4]([CH2:17]OS(C)(=O)=O)[CH2:3]1.[CH3:23][N:24](C=O)C.[C-]#N.[Na+]>O>[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:5][CH:4]([CH2:17][C:23]#[N:24])[CH2:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 57988762HCID 57988762, compound

Product 1

HCID 57988764HCID 57988764, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
52.5 °C

Procedure

A mixture of methanesulfonic acid 5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-ylmethyl ester (prepared as given in Example B1)(0.9 g, 2.66 mmol), DMF (5 ml) and sodium cyanide (0.19 g, 4.0 mol) were heated to 50-55° C. and stirred for 20 hrs. To this reaction mixture water (50 ml) was added and extracted with ethyl acetate (3×20 ml), organic layer was washed with saturated brine solution (20 ml). The organic layer was dried over Na2SO4 and evaporated to obtain [5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-yl]-acetonitrile (0.65 g, 91%) as brownish sticky mass.

Workup

  1. extractionextracted with ethyl acetate (3×20 ml), organic layer
  2. washwas washed with saturated brine solution (20 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-d7f605a6fcc742e5a237761ad4b9a533
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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