Urea → 5,7-dichloroquinazoline-2,4(1H,3H)-dione

HRID 2294173Notes

Reaction equation

HRID 2294173 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4](O)=[O:5].[NH2:13][C:14](N)=[O:15]>>[Cl:12][C:7]1[CH:8]=[C:9]([Cl:11])[CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:13][C:14](=[O:15])[NH:1]2

Participants

3

Reactant 2

HCID 1176UreaHCID 2904984,6-Dichloroanthranilic acid

Product 1

HCID 15088015,7-dichloroquinazoline-2,4(1H,3H)-dioneYield 40%

Conditions

Temperature
160 °C

Procedure

A mixture of 2 g (10 mmol) of 2-amino-4,6-dichlorobenzoic acid and 1.6 g (30 mmol) 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. 880 mg (40%) of 5,7-dichloro-1,2,3,4-tetrahydroquinazoline-2,4-dione were obtained as beige crystals;

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-fa0e83aa2bac44debe53466418448446
Source dataset
uspto-grants-1997_11
Patent number
US05688803

Reaction notes

Loading…