Sodium methanethiolate → 4-Sulfanylbenzene-1,3-dicarbonitrile

HRID 6019

Reaction equation

HRID 6019 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1I)[C:6]#[N:7])#[N:2].C[S-:13].[Na+]>CN(C)P(N(C)C)(N(C)C)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[SH:13])[C:6]#[N:7])#[N:2]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 125572024-Iodoisophthalonitrile

Product 1

HCID 147953364-Sulfanylbenzene-1,3-dicarbonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
80 °C

Procedure

Under argon, 3.03 g (12.10-3 mol) of 3-cyano-4-iodobenzonitrile and 3.36 g (48.10-3 mol) of sodium thiomethylate are dissolved in 80 ml of anhydrous hexamethylphosphoramide and the solution obtained is then heated at 80° C. for 45 minutes. The resulting reaction medium is hydrolyzed in an ice/1N HCl mixture and then extracted with methylene chloride. The organic phase is washed with water and then dried over magnesium sulfate and evaporated under reduced pressure to give 1.55 g (yield: 81%) of the expected product.

Workup

  1. customthe solution obtained
  2. customThe resulting reaction medium
  3. extractionextracted with methylene chloride
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2500ab4f295340a7972ceb2a034d096d
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Linked notes

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