Sodium Sulfide → HCID 178467479, compound

HRID 1500103Notes

Reaction equation

HRID 1500103 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([O:22][CH2:23][CH3:24])[N:3]=1.[S-2:25].[Na+].[Na+]>CN(C=O)C>[CH2:23]([O:22][C:4]1[C:5]([C:20]#[N:21])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:7]([C:8]#[N:9])=[C:2]([SH:25])[N:3]=1)[CH3:24]

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 58297349HCID 58297349, compound

Product 1

HCID 178467479HCID 178467479, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g (2.909 mmol) of 2-chloro-6-ethoxy-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile is initially charged in 7.5 ml of DMF, 454 mg (5.818 mmol) of sodium sulphide are added and the mixture is stirred at room temperature overnight. The mixture is concentrated, the residue is triturated with acetonitrile and the solid is filtered off and dried under high vacuum. This gives 230 mg (24% of theory) of the target compound.

Workup

  1. concentrationThe mixture is concentrated
  2. customthe residue is triturated with acetonitrile
  3. filtrationthe solid is filtered off
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-5a6daa4984264769b9fbef436645c3db
Source dataset
uspto-grants-2015_12
Patent number
US09205077B2

Reaction notes

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