Potassium Cyanide → HCID 18382508, compound

HRID 2297603Notes

Reaction equation

HRID 2297603 reaction equation
[CH2:1]([N:8]1[C:12]2[C:13](=[O:24])[N:14]([CH2:22][CH3:23])[C:15]3[N:16]([N:17]=[C:18]([CH2:20]Br)[N:19]=3)[C:11]=2[N:10]=[C:9]1[CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:30]#[N:31].[K+]>O.C(O)C>[CH2:1]([N:8]1[C:12]2[C:13](=[O:24])[N:14]([CH2:22][CH3:23])[C:15]3[N:16]([N:17]=[C:18]([CH2:20][C:30]#[N:31])[N:19]=3)[C:11]=2[N:10]=[C:9]1[CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 15432862HCID 15432862, compound

Product 1

HCID 18382508HCID 18382508, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

0.46 g of 6-benzyl-2-bromomethyl-7-cyclopentyl-4-ethyl-imidazo[4.5-e]-s-triazolo[1.5-a]pyrimidin-5-one (for preparation see Synthesis example 1) are added to a solution of 0.72 g of KCN in 0.7 ml of water and 2.4 ml of ethanol heated to boiling. The mixture is boiled for a further 30 minutes until the reaction is complete. For working up the mixture is diluted with 10 ml of water and extracted with 15 ml of dichloromethane. The organic phase is separated off, washed with saturated sodium chloride solution and dried over magnesium sulphate. The solvent is distilled off and the residue remaining is purified by chromatography on silica gel (dichloromethane:methanol 99:1). 0.3 g of the title compound is obtained in the form of a colourless solid.

Workup

  1. temperatureheated to boiling
  2. extractionextracted with 15 ml of dichloromethane
  3. customThe organic phase is separated off
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. distillationThe solvent is distilled off
  7. customthe residue remaining is purified by chromatography on silica gel (dichloromethane:methanol 99:1)

Sources & evidence

ORD record
ord-b7af9fdc1bb04865b26ec409324f24be
Source dataset
uspto-grants-2002_12
Patent number
US06492377B1

Reaction notes

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