Benzoyl chloride → 5-benzoyl-1,3,6-trimethyl-2,4(1H,3H)-Pyrimidinedione

HRID 1912353Notes

Reaction equation

HRID 1912353 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](=[O:9])[N:4]([CH3:10])[C:3]1=[O:11].[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[C:12]([C:6]1[C:5](=[O:9])[N:4]([CH3:10])[C:3](=[O:11])[N:2]([CH3:1])[C:7]=1[CH3:8])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 260751,3,6-Trimethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 8023085-benzoyl-1,3,6-trimethyl-2,4(1H,3H)-PyrimidinedioneYield 28.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1,3,6-trimethyl-compound 2 (12.3 g, 80 mmol), benzoyl chloride (11.5 g, 9.5 mL, 82 mmol) and anhydrous zinc chloride (10.8 g, 79 mmol) in toluene (100 mL) was heated to reflux for 6 h. The mixture was poured over ice (200 g), and the separated toluene layer was concentrated in vacuo. The crude residue was purified by flash chromatography to yield 3 (5.8 g, 28%): mp 132-134° C.; MS (ES+) (m/z): [M+1]+ calculated for C14H15N2O3, 259.28. found 259.09. This compound matched analytical data as reported (see, e.g., Tsupak et al., Khimiya Geterotsiklicheskikh Soedinenii. 7:1096-1102 (2003)).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. concentrationthe separated toluene layer was concentrated in vacuo
  4. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9da699f9e44640b696514f304695e114
Source dataset
uspto-grants-2013_12
Patent number
US08609661B2

Reaction notes

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