Urea → 7-NITROQUINAZOLINE-2,4(1H,3H)-DIONE

HRID 2294180Notes

Reaction equation

HRID 2294180 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:14][C:15](N)=[O:16]>>[N+:11]([C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:6])[NH:14][C:15](=[O:16])[NH:1]2)=[CH:7][CH:8]=1)([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 1176UreaHCID 120764-Nitroanthranilic acid

Product 1

HCID 33981137-NITROQUINAZOLINE-2,4(1H,3H)-DIONEYield 85.8%

Conditions

Temperature
160 °C

Procedure

A mixture of 5 g (0.027 mol) of 2-amino-4-nitrobenzoic acid and 16.5 g (0.27 mol) of urea was heated to 160° C. for 2 hrs. and at 180° C. for a further 2 hrs. The resulting brown mass was triturated with 200 ml of methanol, filtered off and dried in a vacuum. 4.8 g (80%) of 7-nitro-1,2,3,4-tetrahydro-quinazoline-2,4-dione were obtained as a white solid;

Workup

  1. customThe resulting brown mass was triturated with 200 ml of methanol
  2. filtrationfiltered off
  3. customdried in a vacuum

Sources & evidence

ORD record
ord-03ea58366406485ebc7c02c3c366467c
Source dataset
uspto-grants-1997_11
Patent number
US05688803

Reaction notes

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