Sodium Cyanide → HCID 18622134, compound

HRID 1861939Notes

Reaction equation

HRID 1861939 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[CH:8][C:7]=1[F:23]>CS(C)=O.O>[C:1]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[CH:8][C:7]=1[F:23])#[N:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 18621739N-(4-bromomethyl-3-fluorophenyl)phthalimide

Product 1

HCID 18622134HCID 18622134, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of sodium cyanide (99 mg) in dimethyl sulfoxide (5 ml), a solution of the compound (605 mg) obtained in Example 249 in dimethyl sulfoxide (10 ml) was added dropwise at 60° C. and stirred at 60° C. for 40 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate-diethyl ether (1:1); thereafter, the organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=6:4) to give 164 mg of the titled compound (yield, 32%).

Workup

  1. extractionextracted with ethyl acetate-diethyl ether (1:1)
  2. washthereafter, the organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-35946c5ccef64ea3b8efd537c827381e
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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