Chlorosuccinimide → 5-chloro-6-ethyl-2-phenyl-4(3H)-pyrimidinone

HRID 2400102

Reaction equation

HRID 2400102 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:6][C:5](=[O:15])[CH:4]=1)[CH3:2].[Cl:16]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:16][C:4]1[C:5](=[O:15])[NH:6][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:8][C:3]=1[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 1356298226-Ethyl-2-phenylpyrimidin-4(1H)-one

Product 1

HCID 1358375365-chloro-6-ethyl-2-phenyl-4(3H)-pyrimidinoneYield 87.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 7.81 g (39.1 mmol) of 6-ethyl-2-phenyl-4(3H)-pyrimidinone and 5.80 g (43.4 mmol) of N-chlorosuccinimide in 100 mL of glacial acetic acid was heated at 90° C. for 4 h. The mixture was cooled, poured onto crushed ice and allowed to stand until the ice had melted. The mixture was filtered and the solid collected was washed with water and a little ether. The solid was dried in a vacuum oven at 50° C. to afford 7.99 g of 5-chloro-6-ethyl-2-phenyl-4(3H)-pyrimidinone (an intermediate for compound 172) as a white solid. 1H-NMR (d6-DMSO) 1.30(3H,t), 2.8(2H,q), 7.6(3H,m), 8.2(2H.m).

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured
  3. customonto crushed ice
  4. filtrationThe mixture was filtered
  5. customthe solid collected
  6. washwas washed with water
  7. customThe solid was dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-1c9d2da34322497cb55088a39411c298
Source dataset
uspto-grants-1995_09
Patent number
US05453414

Linked notes

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