Sodium Cyanide → HCID 19437357, compound

HRID 1352840Notes

Reaction equation

HRID 1352840 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4](C=O)=[CH:3][CH:2]=1.[C-:15]#[N:16].[Na+].[C:18](=[O:21])([O-])[O-:19].[NH4+].[NH4+]>C(O)C>[C:9]1([C:1]2[CH:2]=[CH:3][C:4]([NH:16][CH2:15][C:18]([OH:19])=[O:21])=[CH:5][CH:6]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 517111Ammonium Carbonate

Product 1

HCID 19437357HCID 19437357, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-biphenylcarboxaldehyde (4.6 g 25 mmol), sodium cyanide (3.68 g 75 mmol) and ammonium carbonate (9.60 g 100 mmol) in 50% aqueous ethanol (175 ml) was heated at 50° C. for 20 hours. The reaction mixture was cooled, concentrated under reduced pressure and acidified to pH 2.0 with concentrated hydrochloric acid (fume hood). The intermediate 4-(4-phenylphenyl)-2,5-imidazolinedione was collected by filtration, washed with dilute (0.5%) HCl and dried before using as crude in the next stage. (Filtrates were retained and treated with sodium hypochlorite solution before disposal) The intermediate 4-(4-phenylphenyl)-2,5-imidazolinedione was refluxed in 16% aqueous sodium hydroxide (100 ml, 16% w/v) for 24 h. The reaction mixture was then filtered, cooled, diluted with water (100 ml) and then shaken with ethyl acetate and separated. The aqueous solution was adjusted to pH 5.1 with concentrated hydrochloric acid and the solid obtained collected by filtration, washed with a little water and dried to give 4-phenylphenylglycine (2.36 g, 42%). 1H nmr (d6 DMSO) consistent with desired product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. filtrationThe intermediate 4-(4-phenylphenyl)-2,5-imidazolinedione was collected by filtration
  4. washwashed
  5. additionwith dilute (0.5%) HCl
  6. customdried
  7. addition(Filtrates were retained and treated with sodium hypochlorite solution before disposal) The intermediate 4-(4-phenylphenyl)-2,5-imidazolinedione
  8. temperaturewas refluxed in 16% aqueous sodium hydroxide (100 ml, 16% w/v) for 24 h
  9. filtrationThe reaction mixture was then filtered
  10. temperaturecooled
  11. additiondiluted with water (100 ml)
  12. customseparated
  13. customthe solid obtained
  14. filtrationcollected by filtration
  15. washwashed with a little water
  16. customdried

Sources & evidence

ORD record
ord-66300468063b4c289184f6bc1d133e91
Source dataset
uspto-grants-2007_05
Patent number
US07220781B2

Reaction notes

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