Cyanide → HCID 20270258, compound

HRID 485436Notes

Reaction equation

HRID 485436 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]=2[CH2:11]Br)[CH:5]=[CH:6][CH:7]=1.[C-:20]#[N:21]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]=2[CH2:11][C:20]#[N:21])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5975CyanideHCID 13490403HCID 13490403, compound

Product 1

HCID 20270258HCID 20270258, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.16 G. 2-(3'-bromophenylthio)-5-nitrobenzyl bromide is refluxed in 50 cc. ethanol and 2.4 g. of cyanide ion exchange resin for 1/2 hour. The mixture is filtered hot and the resin washed with ethyl acetate. The combined organic filtrates are evaporated to dryness to yield 1.85 g. of crude residue which is chromatographed on silica gel. Elution with benzene affords 800 mg. of the desired compound.

Workup

  1. filtrationThe mixture is filtered hot
  2. washthe resin washed with ethyl acetate
  3. customThe combined organic filtrates are evaporated to dryness
  4. customto yield 1.85 g
  5. customof crude residue which is chromatographed on silica gel
  6. washElution with benzene
  7. customaffords 800 mg

Sources & evidence

ORD record
ord-e03b3a270d3b436f9af373d81af22d90
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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