Potassium Cyanide → HCID 14882502, compound

HRID 330139Notes

Reaction equation

HRID 330139 reaction equation
Cl[CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][CH:4]=1.[C-:22]#[N:23].[K+].O1CCOCCOCCOCCOCCOCC1>C(#N)C>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[C:3]([CH2:2][C:22]#[N:23])[CH:11]=3)[CH:7]=[CH:8]2)(=[O:13])=[O:14])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 14882501HCID 14882501, compound

Product 1

HCID 14882502HCID 14882502, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-chloromethyl-1-(4-methylphenylsulfonyl)indole (21.5 g) in acetonitrile (224 ml) was treated with potassium cyanide (8.8 g) and 1,4,7,10,13,16-hexaoxacyclooctadecane (3.6 g) and stirred at room temperature under a nitrogen atmosphere for 18 hr. The solution was poured onto ice and extracted with methylene chloride. The organic phase was washed with water and brine, dried (MgSO4) and evaporated. The resultant amber oil was purified by flash chromatography, eluting with 1:5 ethyl acetate:hexane, to give 1-(4-methylphenylsulfonyl)indole-6-acetonitrile (14.4 g, 76%) as a white powder; partial NMR (80 MHz, CDCl3): 2.34(s, 3H, ArCH3), 3.84(s, 2H, NCCH2), 6.62(dd, 1H, H3 -indole), 7.94(m, 1H, H7 -indole)

Workup

  1. additionThe solution was poured onto ice
  2. extractionextracted with methylene chloride
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe resultant amber oil was purified by flash chromatography
  7. washeluting with 1:5 ethyl acetate

Sources & evidence

ORD record
ord-3c766acca61744418cc1e85e096ffc9d
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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