Hydrochloric Acid → 5-[4-(Hydroxymethyl)phenyl]imidazolidine-2,4-dione

HRID 848845Notes

Reaction equation

HRID 848845 reaction equation
O[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[C:11](=[O:14])([O-])[O-].[NH4+:15].[NH4+:16].[C-]#N.[Na+].Cl.[CH2:21]([OH:23])C>O>[OH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([CH:2]2[NH:16][C:21](=[O:23])[NH:15][C:11]2=[O:14])=[CH:4][CH:5]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 5563304-(Hydroxymethyl)benzaldehyde

Product 1

HCID 205648085-[4-(Hydroxymethyl)phenyl]imidazolidine-2,4-dioneYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred mixture of p-hydroxymethylbenzaldehyde (10.0 g., 0.0735 mole) and ammonium carbonate (17.1 g., 0.15 mole) in 110 ml. of 60% ethanol heated to 50° C. there was added dropwise sodium cyanide (4.0 g., 0.081 mole) dissolved in 10 ml. water. The mixture was stirred and heated to 55°-60° C. for three hours and then the temperature raised to 85° C. for one hour. After cooling in an ice bath, the pH of the solution was brought to 6 by the addition of concentrated hydrochloric acid. Upon overnight cooling, the solid which had precipitated was filtered, washed with cold water, and dried. The 5-(p-hydroxymethylphenyl)hydantoin (11.0 g., 72% yield), m.p. 189°-196° (dec.), was used to prepare the amino acid without further purification.

Workup

  1. dissolutiondissolved in 10 ml
  2. temperatureheated to 55°-60° C. for three hours
  3. temperatureAfter cooling in an ice bath
  4. temperatureUpon overnight cooling
  5. customthe solid which had precipitated
  6. filtrationwas filtered
  7. washwashed with cold water
  8. customdried

Sources & evidence

ORD record
ord-44bd6f39092a490a97f2269492756cec
Source dataset
uspto-grants-1981_10
Patent number
US04297489

Reaction notes

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