Benzoyl chloride → HCID 2785824, compound

HRID 1884547Notes

Reaction equation

HRID 1884547 reaction equation
[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][C:6](=[O:7])[N:5]([CH3:11])[C:3]1=[O:4].[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:12]([CH:8]1[C:9](=[O:10])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:11])[C:6]1=[O:7])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 69860Dimethylbarbituric acid

Product 1

HCID 2785824HCID 2785824, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 1,3-dimethylbarbituric acid (5 g, 32.02 mmol), 4-dimethylaminopyridine (4.74 g, 38.79 mmol) in dry CH2Cl2 (75 ml) was cooled to 0° C. and benzoyl chloride (4.95 g, 35.22 mmol) added dropwise in 15 min. The reaction mixture was stirred for 3 h at room temperature, diluted with CH2Cl2 (150 ml) and washed with 2 N HCl solution (40 ml). The organic phase was dried over MgSO4 and evaporated. The residue was crystallised from diisopropylether then recrystallised from MeOH, giving 5-benzoyl-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione 3 (5.32 g, 64%).

Workup

  1. washwashed with 2 N HCl solution (40 ml)
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated
  4. customThe residue was crystallised from diisopropylether
  5. customthen recrystallised from MeOH

Sources & evidence

ORD record
ord-2b42ef97718a48a0823b4de5c04dc5db
Source dataset
uspto-grants-2004_07
Patent number
US06765089B1

Reaction notes

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