Potassium Cyanide → HCID 19897885, compound

HRID 1197172Notes

Reaction equation

HRID 1197172 reaction equation
Cl[CH2:2][C:3]1[C:15]2[C:14]3[C:9](=[C:10]([CH3:17])[CH:11]=[CH:12][C:13]=3[CH3:16])[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[C-:28]#[N:29].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[C:28]([CH2:2][C:3]1[C:15]2[C:14]3[C:9](=[C:10]([CH3:17])[CH:11]=[CH:12][C:13]=3[CH3:16])[N:8]([S:18]([C:21]3[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=3)(=[O:20])=[O:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:29]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 19897872HCID 19897872, compound

Product 1

HCID 19897885HCID 19897885, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5.39 g of 4-chloromethyl-5,8-dimethyl-9-p-toluenesulfonylcarbazole obtained in Example 1(3), 1.82 g of potassium cyanide and 1.79 g of 18-crown-6 in 80 ml of acetonitrile was stirred at room temperature overnight. The reaction solution was poured into ice water and extracted with ethyl acetate, and the organic layer was washed, in turn, with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chlorided solution and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave 5.21 g of 4-cyanomethyl-5,8-dimethyl-9-p-toluenesulfonylcarbazole.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed, in turn, with a saturated aqueous sodium bicarbonate solution
  3. dry with materiala saturated aqueous sodium chlorided solution and dried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a7305e562e0e4912be13d71ca10972a4
Source dataset
uspto-grants-1992_05
Patent number
US05116995

Reaction notes

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