Hydrochloric Acid → 5-(4-Phenoxyphenyl)-1,3-diazinane-2,4,6-trione

HRID 1386642Notes

Reaction equation

HRID 1386642 reaction equation
O(C)[Na].[O:4]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:22]([O:24]C)=O)[C:18]([O:20]C)=O)=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:26][C:27]([NH2:29])=[O:28].Cl>>[O:4]([C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[C:18](=[O:20])[NH:29][C:27](=[O:28])[NH:26][C:22]2=[O:24])=[CH:15][CH:16]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 15540880Dimethyl 2-(4-phenoxyphenyl)malonateHCID 178418582HCID 178418582, compound

Product 1

HCID 116737785-(4-Phenoxyphenyl)-1,3-diazinane-2,4,6-trioneYield 84.1%

Conditions

Temperature
0 °C

Procedure

To a NaOCH3 solution (prepared by allowing 0.23 g of Na metal to react with 7.2 mL dry CH3OH) was added dimethyl 2-(4-phenoxyphenyl)malonate (1.0 g, 3.33 mmol) followed by urea (0.4 g, 6.66 mmol). The resulting white reaction mixture was refluxed for 24 hours and then cooled to 0° C. and acidified with 3N HCl. The white solids were filtered and washed with water and dried to give 900 mg of crude product. This was further purified by trituration with EtOAc/hexanes (1:1) to afford 5-(4-phenoxyphenyl)pyrimidine-2,4,6-trione as a white powder (830 mg): 1H NMR (400 mHz, CDCl3) 3:2 keto/enol form δ 11.38 (2×NH keto form, s), 10.58 (2×NH enol form, s), 7.46-6.91(9H, m), 4.85 (H-5, s); HRMS Calcd for C16H12N2O4 296.0796; Found 296.0806.

Workup

  1. temperatureThe resulting white reaction mixture was refluxed for 24 hours
  2. filtrationThe white solids were filtered
  3. washwashed with water
  4. customdried
  5. customto give 900 mg of crude product
  6. customThis was further purified by trituration with EtOAc/hexanes (1:1)

Sources & evidence

ORD record
ord-29594cba50a449509d2aab90175e8084
Source dataset
uspto-grants-2001_07
Patent number
US06265578B1

Reaction notes

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