Sodium Cyanide → HCID 22111028, compound

HRID 565663Notes

Reaction equation

HRID 565663 reaction equation
Br[CH2:2][C:3]1([CH3:18])[CH2:7][C:6]2[C:8]([CH3:17])=[C:9]([NH:14][CH:15]=[O:16])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[C-:19]#[N:20].[Na+]>CS(C)=O.O>[C:19]([CH2:2][C:3]1([CH3:18])[CH2:7][C:6]2[C:8]([CH3:17])=[C:9]([NH:14][CH:15]=[O:16])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1)#[N:20]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 10495279HCID 10495279, compound

Product 1

HCID 22111028HCID 22111028, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of N-(2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-5-yl)formamide (20 g) and sodium cyanide (17 g) in dimethyl sulfoxide (100 mL) was stirred under argon gas at 100° C. for 13 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water and saturated aqueous NaCl, dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/diisopropyl ether to provide 14 g of the title compound. Yield 86%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-b46d7504645e423084a87d8890c4bc28
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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