Urea → HCID 20195530, compound

HRID 653055Notes

Reaction equation

HRID 653055 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].[C:5]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:6][C:7](C)=O.[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)([O-:16])=[O:15]>C(O)C.Cl>[N+:14]([C:17]1[CH:18]=[C:19]([CH:20]2[C:6]([C:5]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][NH:4][C:2](=[O:3])[NH:1]2)[CH:22]=[CH:23][CH:24]=1)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 1176UreaHCID 74493-NitrobenzaldehydeHCID 8868Ethyl Acetoacetate

Product 1

HCID 20195530HCID 20195530, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
-20 °C

Procedure

A mixture of urea (52 mmol), ethyl acetoacetate (78 mmol) and m-nitrobenzaldehyde (49 mmol) in absolute ethanol (30 mL) and concentrated hydrochloric acid (10 drop) was heated to reflux for 4.5 hours. Upon cooling to -20° C., a crude product crystallized. The crude product was recrystallized from isopropanol to afford the desired product as a white solid (m.p. 230.5°-233° C.).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 hours
  3. customa crude product crystallized
  4. customThe crude product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-9314c57a93be4e3aa4484e5bb1f7f424
Source dataset
uspto-grants-1987_06
Patent number
US04675321

Reaction notes

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