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

HRID 552372

Reaktionsgleichung

Reaktionsgleichung von HRID 552372
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 196044425-Nitroquinazoline-2,4(1H,3H)-dioneAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b7956213360d490fbb2be25964f1dad5
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951814B2

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