Hydrochloric Acid → 5-(4-Chlorophenyl)pyrimidin-2(1H)-one

HRID 1578

Reaction equation

HRID 1578 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH:11]N(C)C)[CH:9]=O)=[CH:4][CH:3]=1.[NH2:15][C:16]([NH2:18])=[O:17].Cl.[Cl-].[NH4+]>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:11]=[N:15][C:16](=[O:17])[NH:18][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 25517Ammonium ChlorideHCID 34489722-(4-Chlorophenyl)-3-(dimethylamino)acrylaldehyde

Product 1

HCID 136055385-(4-Chlorophenyl)pyrimidin-2(1H)-oneYield 29.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-(4-chlorophenyl)dimethylaminopropenal (Example 145a) (5.13 g), urea (2.4 g), concentrated HCl (10 ml), water (4 ml) and ethanol (150 ml) was refluxed for 4 hours. After cooling to room temperature concentrated ammonium chloride was added until the pH was 7. The resulting yellow solid was filtered off and dried yielding 1.5 g of 5-(4-chlorophenyl)-2-pyrimidinone.

Workup

  1. temperaturewas refluxed for 4 hours
  2. additionwas added until the pH was 7
  3. filtrationThe resulting yellow solid was filtered off
  4. customdried

Sources & evidence

ORD record
ord-50a47b176604482395560ff8f1a4f880
Source dataset
uspto-grants-1998_03
Patent number
US05726176

Linked notes

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