Potassium Cyanide → 5-(4-Cyano-2-vinylphenyl)hydantoin

HRID 343945Notes

Reaction equation

HRID 343945 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([CH:11]=[CH2:12])[CH:4]=1)#[N:2].[C-]#N.[K+].[C:16](=[O:19])([O-])[O-].[NH4+:20].[NH4+:21].[CH2:22]([OH:24])C.O>>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[NH:21][C:22](=[O:24])[NH:20][C:16]2=[O:19])=[C:5]([CH:11]=[CH2:12])[CH:4]=1)#[N:2]

Participants

5

Reactant 4

HCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 19096565Water ethanolHCID 54049649HCID 54049649, compound

Product 1

HCID 700787825-(4-Cyano-2-vinylphenyl)hydantoin

Conditions

Temperature
85 °C

Procedure

A stirred mixture of 4-cyano-2-vinylbenzaldehyde (0.24 g, 1.53 mmol), potassium cyanide (0.2 g, 3.06 mmol) and ammonium carbonate (0.59 g, 6.12 mmol) in ethanol-water (1:1, 6 ml) was heated to 85° C. for 17 hours following the procedure described in Example 1 part (ii). The crude solid obtained after extraction was chromatographed on flash silica eluting with ethyl acetate-hexane (4:1) to give 5-(4-cyano-2-vinylphenyl)hydantoin as a gum.

Workup

  1. customThe crude solid obtained
  2. extractionafter extraction
  3. customwas chromatographed on flash silica eluting with ethyl acetate-hexane (4:1)

Sources & evidence

ORD record
ord-87c0a557a4cd4beb8dc2f995764c8f92
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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