Acetic Acid → HCID 178518377, compound

HRID 1666650Notes

Reaction equation

HRID 1666650 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](O)=[O:5].C(O)(=O)C.[O-:16][C:17]#[N:18].[K+].[OH-].[Na+]>O>[Cl:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[C:17]([OH:16])[N:18]=[C:4]2[OH:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 124762-Amino-5-chlorobenzoic acidHCID 14798Sodium HydroxideHCID 11378442Potassium cyanate

Product 1

HCID 178518377HCID 178518377, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 2-amino-5-chlorobenzoic acid (25.3 g), acetic acid (9.0 mL), and water (650 mL) was added an aqueous solution (130 mL) of potassium cyanate (15.5 g), and the mixture was stirred at room temperature for 2 days. Sodium hydroxide (59 g) was added over 30 min. Water (100 mL) was added, and then the precipitated solids were collected by filtration. The resulting solids were suspended in water (700 mL), followed by addition of 4 M hydrochloric acid (55 mL), and then the precipitated solids were collected by filtration to obtain 6-chloroquinazoline-2,4-diol (19.1 g).

Workup

  1. filtrationthe precipitated solids were collected by filtration
  2. additionfollowed by addition of 4 M hydrochloric acid (55 mL)
  3. filtrationthe precipitated solids were collected by filtration

Sources & evidence

ORD record
ord-2f0b98f013bd41d78891fc6229fd72ed
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

Loading…