Sodium Sulfide → HCID 18616045, compound

HRID 1263398Notes

Reaction equation

HRID 1263398 reaction equation
[S-2].[Na+].[Na+].[CH3:4][C:5]1[C:12]([C:13]#[N:14])=[C:11]([S:15]C#N)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]>O.CO>[CH3:4][C:5]1[C:12]([C:13]#[N:14])=[C:11]([SH:15])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Participants

5

Reactant 2

HCID 14804Sodium SulfideHCID 18616033HCID 18616033, compound

Product 1

HCID 18616045HCID 18616045, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

At 25-35° C., a solution of 110.5 g (0.85 mol) of 60 percent pure sodium sulfide in 425 ml of water was added dropwise to a solution of 170 g (0.85 mol) of 2-methyl-4-thiocyanoisophthalonitrile in 850 ml of methanol, and the mixture was stirred at room temperature for 3 hours. The mixture was then admixed with 1000 ml of water and extracted with methyl tert-butyl ether. The aqueous phase was acidified to pH 1 using HCl, and the thiophenol was extracted with methylene chloride. The extract was washed three times with water, and the organic phase was then separated off, dried over sodium sulfate and concentrated. Yield: 150 g (99%).

Workup

  1. extractionextracted with methyl tert-butyl ether
  2. extractionthe thiophenol was extracted with methylene chloride
  3. washThe extract was washed three times with water
  4. customthe organic phase was then separated off
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c7958e48ef1409c8d4a193feb6a9c07
Source dataset
uspto-grants-2003_04
Patent number
US06541423B1

Reaction notes

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