Urea → 5-Nitroquinazoline-2,4(1H,3H)-dione

HRID 552372

Reaction equation

HRID 552372 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=O.[NH2:14][C:15](N)=[O:16]>C(O)(=O)C.O>[N+:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:2]2[C:3]=1[C:4](=[O:6])[NH:14][C:15](=[O:16])[NH:1]2)([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 1176UreaHCID 957952-Amino-6-nitro-benzoic acid

Product 1

HCID 196044425-Nitroquinazoline-2,4(1H,3H)-dioneYield 64.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-amino-6-nitro-benzoic acid (60 g, 329 mmol) and urea (257.3 g, 4285 mmol) in acetic acid (1.65 lit.) was heated to reflux for 24 h. The acetic acid was evaporated under reduced pressure and the residue obtained was diluted with water (2.5 lit). The solid product separated out was filtered and washed with water. The product was collected and dried in an air oven to give 44 g of the product as a yellow solid; 1H NMR (δ ppm, DMSO-d6, 300 MHz): 11.58 (br. s, 1H); 11.55 (br.s, 1H); 7.76 (t, J=8.4, 1H); 7.41 (d, J=7.8, 1H); 7.32 (d, J=8.4, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. customThe acetic acid was evaporated under reduced pressure
  4. customthe residue obtained
  5. customThe solid product separated out
  6. filtrationwas filtered
  7. washwashed with water
  8. customThe product was collected
  9. customdried in an air oven

Sources & evidence

ORD record
ord-b7956213360d490fbb2be25964f1dad5
Source dataset
uspto-grants-2011_05
Patent number
US07951814B2

Linked notes

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