Dichloroacetic Acid → 5-Dichloroacetyl-1,3-Dimethyl-2,4,6(1H,3H,5H)-Pyrimidinetrione

HRID 1884550Notes

Reaction equation

HRID 1884550 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].[Cl:12][CH:13]([Cl:17])[C:14](O)=[O:15].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:12][CH:13]([Cl:17])[C:14]([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:15]

Participants

6

Reactant 3

HCID 6597Dichloroacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 69860Dimethylbarbituric acid

Product 1

HCID 235061885-Dichloroacetyl-1,3-Dimethyl-2,4,6(1H,3H,5H)-PyrimidinetrioneYield 63.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1,3-dimethylbarbituric acid (5.00 g, 32.05 mmol), dichloroacetic acid (6.19 g, 48.03 mmol), 4-dimethylaminopyridine (1.95 g, 16.01 mmol) in dry CH2Cl2 (30 ml) was cooled to 0° C. and 1,3-dicyclohexylcarbodiimide (7.26 g, 35.22 mmol) added. The reaction mixture was stirred at room temperature overnight and filtered. The solid was washed with CH2Cl2 (150 ml) and the combined solution was washed with 2 N HCl solution (40 ml). The organic phase was dried over MgSO4 and evaporated. The residue was crystallised from MeOH giving 5-dichloroacetyl-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione 7 (5.41 g, 63%).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with CH2Cl2 (150 ml)
  3. washthe combined solution was washed with 2 N HCl solution (40 ml)
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated
  6. customThe residue was crystallised from MeOH

Sources & evidence

ORD record
ord-e4f3713ebaf24d219ff7510f365b0ca0
Source dataset
uspto-grants-2004_07
Patent number
US06765089B1

Reaction notes

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