Malonic Acid → HCID 59717185, compound

HRID 75666Notes

Reaction equation

HRID 75666 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][CH3:13])=[O:11].[C:14]([OH:20])(=O)[CH2:15][C:16]([OH:18])=O.C(OC(=O)C)(=O)C.C(Cl)(=O)C>CCCCCC.O.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14](=[O:20])[CH2:15][C:16](=[O:18])[N:12]([CH3:13])[C:10]1=[O:11]

Participants

7

Reactant 4

HCID 867Malonic AcidHCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 597173511-(2-Fluoro-4-iodophenyl)-3-methylurea

Product 1

HCID 59717185HCID 59717185, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 22272177Toluene waterSolvent

Conditions

Temperature
65 °C

Procedure

Under a nitrogen atmosphere, to 1-(2-fluoro-4-iodophenyl)-3-methylurea 63 (87.9 g) obtained in Step 1 and malonic acid 4 (31.1 g) were added acetic anhydride (264 ml) and acetyl chloride (42.5 ml), and the mixture was stirred at 65° C. for 3 hrs. After allowing to cool to room temperature, the reaction mixture was added dropwise to water-toluene [2:1 (volume ratio), 800 ml] with stirring, and hexane (132 ml) was successively added. The precipitated crystals were collected by filtration and dried to give 1-(2-fluoro-4-iodophenyl)-3-methylpyrimidine-2,4,6-trione 64 (75.3 g, yield 69.5%) as pale-yellow crystals.

Workup

  1. temperatureto cool to room temperature
  2. stirringwith stirring
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-00c21218615e4e39b1adb70265ec2921
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Reaction notes

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