Potassium Cyanide → 91481-24-2

HRID 1681808Notes

Reaction equation

HRID 1681808 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[Cl-:10].[NH4+:11].[C-:12]#[N:13].[K+]>CO.O>[ClH:10].[NH2:11][CH:5]([C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[CH:3]=1)[C:12]#[N:13]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 25517Ammonium ChlorideHCID 765833-Bromobenzaldehyde

Product 1

HCID 1797964391481-24-2

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 3-bromobenzaldehyde (18.5 g, 0.1 mol) is dissolved in methanol (15 ml) and stirred at room temperature as a solution of ammonium chloride (5.35 g, 0.1 mol) in water (12.5 ml) is added in one portion. After thirty minutes a solution of potassium cyanide (6.5 g, 0.1 mol) in water (12.5 ml) is added in one portion and the reaction stirred overnight. The mixture is then refluxed one hour, allowed to cool, and the separated oil extracted into diethyl ether and treated with an ethereal solution of hydrogen chloride to give a brown solid. This is recrystallized by dissolving in methanol (100 ml), diluting with diethyl ether (450 ml), and refrigerating the solution overnight. The solid obtained is filtered, washed with ether, and dried (3.5 g).

Workup

  1. additionis added in one portion
  2. temperatureThe mixture is then refluxed one hour
  3. temperatureto cool
  4. extractionthe separated oil extracted into diethyl ether
  5. additiontreated with an ethereal solution of hydrogen chloride
  6. customto give a brown solid
  7. customThis is recrystallized
  8. dissolutionby dissolving in methanol (100 ml)
  9. additiondiluting with diethyl ether (450 ml)
  10. customthe solution overnight
  11. customThe solid obtained
  12. filtrationis filtered
  13. washwashed with ether
  14. customdried (3.5 g)

Sources & evidence

ORD record
ord-056bc687e06c4507b0ae3be950f09506
Source dataset
uspto-grants-1992_12
Patent number
US05175153

Reaction notes

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