Urea → 6-Nitro-2,4(1H,3H)-quinazolinedione

HRID 1428869Notes

Reaction equation

HRID 1428869 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].[N+:5]([C:8]1[CH:16]=[C:12]([C:13](O)=[O:14])[C:11](N)=[CH:10][CH:9]=1)([O-:7])=[O:6]>O>[N+:5]([C:8]1[CH:16]=[C:12]2[C:11](=[CH:10][CH:9]=1)[NH:4][C:2](=[O:3])[NH:1][C:13]2=[O:14])([O-:7])=[O:6]

Participants

4

Reactant 2

HCID 1176UreaHCID 120322-Amino-5-nitrobenzoic acid

Product 1

HCID 8169826-Nitro-2,4(1H,3H)-quinazolinedioneYield 94.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Urea (9.89 g, 0.165 mol) and 5-nitroanthranilic acid (6.00 g, 32.9 mmol) were heated to 200° C. with vigorous stirring for 1 h. The melt was allowed to cool to 150° C., and water (150 mL) was slowly added. The resulting slurry was sonicated for 1 h and stirred vigorously for an additional 2 h. It was then cooled to 0° C., and the precipitate was collected and rinsed with water to yield the titled compound (6.43 g, 94% yield). This material was dried in a vacuum oven and used without further purification. This compound did not yield MS data.

Workup

  1. customThe resulting slurry was sonicated for 1 h
  2. stirringstirred vigorously for an additional 2 h
  3. temperatureIt was then cooled to 0° C.
  4. customthe precipitate was collected
  5. washrinsed with water

Sources & evidence

ORD record
ord-4895afe66da145999027cbcb7c2a9558
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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