Formaldehyde → HCID 178519997, compound

HRID 1578312Notes

Reaction equation

HRID 1578312 reaction equation
[C:1]([C:6]1[N:7]=[CH:8][NH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(OCC)=[O:2].[OH-].[Na+].C=O>O>[OH:2][CH2:1][C:6]1[N:7]=[CH:8][NH:9][C:10]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 178470301HCID 178470301, compound

Product 1

HCID 178519997HCID 178519997, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 2.16 g (0.01 mol) of 4-carbethoxy-5-phenylimidazole in 10 ml of water was added 0.8 g (0.02 mol) of sodium hydroxide. The mixture was heated to reflux for 2 hours. To this mixture was added 4 ml of ~ 37% aqueous formaldehyde solution, and the resultant mixture was heated at 60°-65° C. for 8 hours, with stirring. After completion of the reaction, the reaction mixture was cooled and the resultant solid was recovered by filtration, washed with water and recrystallized from ethyl acetate and filtered to give 1.18 g of 4-hydroxymethyl-5-phenylimidazole, m.p. 175°-176° C. Yield 68%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled
  5. filtrationthe resultant solid was recovered by filtration
  6. washwashed with water
  7. customrecrystallized from ethyl acetate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-031a8dc2a001427ba7f76073e83eaa45
Source dataset
uspto-grants-1981_09
Patent number
US04292431

Reaction notes

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