Urea → HCID 178488789, compound

HRID 1380508Notes

Reaction equation

HRID 1380508 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].CC[O-].[Na+].CN(C)[CH:11]=[C:12]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:13](=O)[CH3:14]>C(O)C>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:12]2[C:13]([CH3:14])=[N:1][C:2](=[O:3])[NH:4][CH:11]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1176UreaHCID 2723922Sodium ethoxideHCID 539901024-Dimethylamino-3-(4-methoxyphenyl)-3-buten-2-one

Product 1

HCID 178488789HCID 178488789, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

24.4 g of urea and 120 ml of a 25 percent ethanolic solution of sodium ethylate are added to a solution of 40.0 g of 4-dimethylamino-3-(4-methoxyphenyl)-3-buten-2-one in 120 ml of ethanol. The mixture is heated at the reflux temperature for 8 hours, then cooled to 0° C., and the reaction product is filtered off with suction and washed with cold ethanol. The residue is dissolved in water and, while cooling in ice, is neutralised with dilute hydrochloric acid. The precipitated product is filtered off with suction, washed with water and dried. 19.5 g of 5-(4-methoxyphenyl)-4-methyl-2-(1H)-pyrimidinone are obtained. Melting point 210° C.

Workup

  1. temperatureThe mixture is heated at the reflux temperature for 8 hours
  2. filtrationthe reaction product is filtered off with suction
  3. washwashed with cold ethanol
  4. dissolutionThe residue is dissolved in water
  5. temperaturewhile cooling in ice
  6. filtrationThe precipitated product is filtered off with suction
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-c13d2d9c19694666ab04d374bef008a8
Source dataset
uspto-grants-1986_04
Patent number
US04582834

Reaction notes

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