Sodium Cyanide → HCID 58460221, compound

HRID 1946506Notes

Reaction equation

HRID 1946506 reaction equation
CS(O[CH2:6][CH:7]1[C:12]2[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[C:14]([CH:16]([CH3:18])[CH3:17])=[N:15][C:11]=2[CH2:10][CH2:9][CH2:8]1)(=O)=O.[C-:27]#[N:28].[Na+]>CS(C)=O.O.C(Cl)Cl>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:13]2[C:12]3[CH:7]([CH2:6][C:27]#[N:28])[CH2:8][CH2:9][CH2:10][C:11]=3[N:15]=[C:14]2[CH:16]([CH3:18])[CH3:17])=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 58460218HCID 58460218, compound

Product 1

HCID 58460221HCID 58460221, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21908982Water methylene chlorideSolvent

Procedure

Intermediate 41 (3.8 g) and sodium cyanide (1.41 g) was dissolved in dimethyl sulfoxide (20 mL) and the mixture was stirred at 60° overnight. The reaction was stopped (only 1 g nitrile required) and cooled to RT before diluting with water/DCM. The aqueous was further extracted with DCM, and the combined organic extracts were passed though a hydrophobic frit, reduced in volume in vacuo, and the residue purified by flash column chromatography (0-15% MeOH in DCM, silica, repeated chromatography required). The appropriate fractions were combined to give the title compound (1.57 g).

Workup

  1. extractionThe aqueous was further extracted with DCM
  2. customthe residue purified by flash column chromatography (0-15% MeOH in DCM, silica, repeated chromatography required)

Sources & evidence

ORD record
ord-3c11ff993693457692d547385599f0a8
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

Loading…