Sodium Cyanide → HCID 20148849, compound

HRID 1632624Notes

Reaction equation

HRID 1632624 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][CH:4]([CH2:8]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:3]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C-:26]#[N:27].[Na+]>CS(C)=O>[C:26]([CH2:8][CH:4]1[CH2:5][C:6](=[O:7])[N:2]([CH3:1])[CH:3]1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)#[N:27]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 20148844HCID 20148844, compound

Product 1

HCID 20148849HCID 20148849, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To 42 g. of 1-methyl-2-phenyl-3-tosyloxymethyl-pyrrolidin-5-one in 72.5 ml. of dimethylsulfoxide was slowly added 5.7 g of sodium cyanide at 45° C. The reaction was stirred for 3 hours at 100° C. and then set at ambient temperature for 18 hours. After decanting into 1500 ml. of ice water, the product was extracted with 2:1 chloroform-ether, dried (Na2SO4) filtered, and concentrated in vacuo to provide 19.0 g. of light yellow crystals.

Workup

  1. customat 45° C
  2. waitset at ambient temperature for 18 hours
  3. customAfter decanting into 1500 ml
  4. extractionof ice water, the product was extracted with 2:1 chloroform-ether
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide 19.0 g

Sources & evidence

ORD record
ord-cc29024d2f93435f9bfd3c57101fdacc
Source dataset
uspto-grants-1984_10
Patent number
US04476311

Reaction notes

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