Potassium Cyanide → HCID 14882502, compound

HRID 330189Notes

Reaction equation

HRID 330189 reaction equation
ClC[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]=[CH:6]2.C1O[CH2:38][CH2:37]OCCOCCOCCOCCOC1.[C-]#[N:41].[K+]>C(#N)C>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:11]([CH2:37][C:38]#[N:41])[CH:10]=3)[CH:6]=[CH:7]2)(=[O:14])=[O:13])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 19870553HCID 19870553, compound

Product 1

HCID 14882502HCID 14882502, compoundYield 449.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-chloromethyl-1-(4-methylphenylsulfonyl)indole (11.1 g), 18-crown-6 (1.8 g), and potassium cyanide (4.5 g) in acetonitrile (117 ml) was stirred under a nitrogen atmosphere for 48 hr. The reaction mixture was poured onto ice and extracted with methylene chloride. The organic phase was washed (water, brine), dried (MgSO4), and evaporated to give 1-(4-methylphenylsulfonyl)indole-6-acetonitrile (9.5 g, 98%) as an ivory powder: NMR (80 MHz, CDCl3): 2.33(s, 3H, ArCH3), 3.79(s, 2H, CH2CN), 6.63(d, 1H, H3 -indole), 7.49(s, 1H, H4 -indole), 7.59(d, 1H, H2 -indole).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted with methylene chloride
  3. washThe organic phase was washed (water, brine)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7ce441851dab4993a22347b2719e2205
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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