Cyanide → HCID 20270258, compound

HRID 1074999Notes

Reaction equation

HRID 1074999 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-07dbb8a94b6f425688bf0e11894d9dfe
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

Loading…