Urea → 7-Chloroquinazoline-2,4-diol

HRID 1428809Notes

Reaction equation

HRID 1428809 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:12][C:13](N)=[O:14]>>[Cl:11][C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:12][C:13](=[O:14])[NH:1]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 1176UreaHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 2468587-Chloroquinazoline-2,4-diol

Conditions

Temperature
200 °C

Procedure

A mixture of 2-amino-4-chlorobenzoic acid (2.00 g, 11.6 mmol) and urea (2.80 g, 46.6 mmol) was heated to 200° C. for 1 h. The mixture was allowed to cool to room temperature and the resulting mass was triturated well with water. The product was collected by filtration (2.30 g, 100%). The MS and NMR data are in agreement with those that have been previously described: Organic Process Research & Development, 2003, 7, 700-706. 1H NMR (600 MHz, DMSO-d6): 12.00 (br s, 2H), 8.59-8.53 (m, 1H), 7.93-7.80 (m, 2H).

Workup

  1. temperatureto cool to room temperature
  2. customthe resulting mass was triturated well with water
  3. filtrationThe product was collected by filtration (2.30 g, 100%)

Sources & evidence

ORD record
ord-9355e22a37684994a208374979ca373c
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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