Hydrochloric Acid → 5-(4-Hydroxyphenyl)-5-(2-thienyl)-2,4-imidazolidinedione

HRID 1278253Notes

Reaction equation

HRID 1278253 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=O)=[CH:4][CH:3]=1.[C-]#[N:16].[K+].[C:18](=[O:21])([O-])[O-].[NH4+].[NH4+].[CH:24]([NH2:26])=[O:25].Cl>O>[OH:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]2([C:8]3[S:9][CH:10]=[CH:11][CH:12]=3)[NH:16][C:24](=[O:25])[NH:26][C:18]2=[O:21])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 713FormamideHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 130205054-(Thiophene-2-carbonyl)phenol

Product 1

HCID 30581965-(4-Hydroxyphenyl)-5-(2-thienyl)-2,4-imidazolidinedione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.0 Grams of 2-(4-hydroxybenzoyl)thiophene were heated together with 5.3 g of potassium cyanide, 17.1 g of ammonium carbonate, 20 ml. of formamide and 10 ml. of water in a stainless steel bomb with occasional stirring at 120° C. for 72 hours. The reaction liquid was adjusted to pH 4 with concentrated hydrochloric acid and then mixed with water to form precipitates. The precipitates thus formed were washed with water, filtered and extracted with ethanol while they were hot. The extract was heated together with a small amount of active carbon under reflux, filtered while it was hot and then cooled to obtain 2.0 g of 5-(4-hydroxyphenyl)-5-(2-thienyl)hydantoin in the form of white crystals.

Workup

  1. customThe reaction liquid
  2. customto form
  3. customprecipitates
  4. customThe precipitates thus
  5. customformed
  6. washwere washed with water
  7. filtrationfiltered
  8. extractionextracted with ethanol while they
  9. temperatureThe extract was heated together with a small amount of active carbon
  10. temperatureunder reflux
  11. filtrationfiltered while it
  12. temperaturecooled

Sources & evidence

ORD record
ord-26ef76958c734d008cc104ba6f47a937
Source dataset
uspto-grants-1981_07
Patent number
US04281009

Reaction notes

Loading…