Hydrochloric Acid → HCID 70079778, compound

HRID 343950Notes

Reaction equation

HRID 343950 reaction equation
[CH2:1]([C:5]1[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:6]=1[CH:7]=O)[CH2:2][CH2:3][CH3:4].[C-]#N.[K+].[C:18](=[O:21])([O-])[O-].[NH4+:22].[NH4+:23].Cl.[CH2:25]([OH:27])C.O>>[CH2:1]([C:5]1[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:6]=1[CH:7]1[NH:23][C:25](=[O:27])[NH:22][C:18]1=[O:21])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 19096565Water ethanolHCID 53968182HCID 53968182, compound

Product 1

HCID 70079778HCID 70079778, compound

Conditions

Temperature
85 °C

Procedure

A stirred mixture of 2-butyl-4-cyanobenzaldehyde (0.9 g, 4.8 mmol), potassium cyanide (0.63 g, 9.6 mmol) and ammonium carbonate (1.85 g, 19.2 mmol) in ethanol/water (1:1, 10 ml) was heated with stirring in a sealed vessel at 85° C. overnight. The resulting crude solution was cooled and acidified with 2N hydrochloric acid (10 ml), then extracted with ethyl acetate (3×20 ml), combined, dried, then evaporated to yield a brown oil. Flash chromatography eluting with ethyl acetate/hexane (4:1) gave a pale brown oil lining the flask. It was triturated with ether (20 ml) and filtered off to give 5-(2-butyl-4-cyanophenyl)hydantoin as a white solid.

Workup

  1. temperaturewas heated
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. customdried
  4. customevaporated
  5. customto yield a brown oil
  6. washFlash chromatography eluting with ethyl acetate/hexane (4:1)
  7. customgave a pale brown oil
  8. customIt was triturated with ether (20 ml)
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-1c88759c09774e6fafb9ce75dd86d77f
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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