Potassium Cyanide → HCID 53920755, compound

HRID 1165154Notes

Reaction equation

HRID 1165154 reaction equation
F[B-](F)(F)F.[CH:6](=[N:13][N+:14]1[CH:18]=[CH:17][N:16](N=CC2C=CC=CC=2)[C:15]=1[N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C-]#N.[K+]>CO.O>[CH:6](=[N:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 73867527HCID 73867527, compound

Product 1

HCID 53920755HCID 53920755, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

4.47 g of 1,3-bis(benylideneamino)-2-morpholinoimidazolium tetrafluoroborate are suspended in 50 ml of methanol. A solution of 1.3 g of potassium cyanide in 20 ml of water is added dropwise within 15 minutes while cooling in an ice-bath, whereby a yellow solution results. The solution is stirred at room temperature for an additional 15 minutes, 150 ml of water are added and the mixture is extracted three times with 30 ml of methylene chloride each time. The combined methylene chloride extracts are dried over sodium sulfate, filtered and evaporated in a vacuum. The yellow oil which remains behind as the residue is treated with 70 ml of ice-cold water. Then the mixture is acidified (pH about 1) with 2N hydrochloric acid and subsequently extracted three times with diethyl ether. The colorless, acidic-aqueous phase is treated with 2N sodium hydroxide solution up to an alkaline reaction (pH about 8-9). The resulting pale yellow precipitate is removed by filtration and reprecipitated from methanol/water. There is obtained 1-benzylideneamino-2-morpholinoimidazole of m.p. 59°-61°.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. customwhereby a yellow solution results
  3. extractionthe mixture is extracted three times with 30 ml of methylene chloride each time
  4. dry with materialThe combined methylene chloride extracts are dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in a vacuum
  7. additionis treated with 70 ml of ice-cold water
  8. extractionsubsequently extracted three times with diethyl ether
  9. additionThe colorless, acidic-aqueous phase is treated with 2N sodium hydroxide solution up to an alkaline reaction (pH about 8-9)
  10. customThe resulting pale yellow precipitate is removed by filtration
  11. customreprecipitated from methanol/water

Sources & evidence

ORD record
ord-ce23183f7ac44d289fa1f8fb4d3a8a2d
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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