Urea → 5-Chloroquinazoline-2,4-diol

HRID 2294169Notes

Reaction equation

HRID 2294169 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4](O)=[O:5].[NH2:12][C:13](N)=[O:14]>>[Cl:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:12][C:13](=[O:14])[NH:1]2

Participants

3

Reactant 2

HCID 1176UreaHCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 3340215-Chloroquinazoline-2,4-diolYield 55.5%

Conditions

Temperature
160 °C

Procedure

A mixture of 2.0 g (11 mmol) of 2-amino-6-chlorobenzoic acid and 1.4 g (23 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. 1.2 g (53%) of 5-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione were obtained as white 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-0bf54a60f66f4a54be903b868cdadb7c
Source dataset
uspto-grants-1997_11
Patent number
US05688803

Reaction notes

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