Hydrochloric Acid → 7-Chloro-1-(2-hydroxyethyl)quinazoline-2,4(1H,3H)-dione

HRID 1532429Notes

Reaction equation

[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O.[OH-].[Li+].[O-:17][C:18]#[N:19].[Na+].Cl>O>[OH:1][CH2:2][CH2:3][N:4]1[C:5]2[C:6](=[CH:10][CH:11]=[C:12]([Cl:14])[CH:13]=2)[C:7](=[O:9])[NH:19][C:18]1=[O:17]

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of 2-(2-hydroxyethylamino)-4-chlorobenzoic acid (5.0 g) in water (50 ml) was added lithium hydroxide (1.0 g), was further added sodium cyanate (1.05 g) with maintaining the temperature at about 40° C. The resulting solution was reacted for 2 hours, adjusting the pH 6.0-7.0 with concentrated hydrochloric acid. Then, to the reaction solution was added lithium hydroxide (1.3 g), was further added sodium cyanate (2.1 g) at the same temperature, the resulting solution was reacted for one hour. Then, the reaction mixture was reacted for further 4 hours with adjusting the pH in the same manner as above. After the reaction, to the reaction solution was added lithium hydroxide (1.7 g) and was reacted for further 3 hours. Concentrated hydrochloric acid (5 ml) was added to this reaction solution, the resulting crystal was collected by filtration to give 4.69 g of 1-(2-hydroxyethyl)-7-chloro-2,4(1H, 3H)-quinazolinedione (yield, 84.1%).

Workup

customThe resulting solution was reacted for 2 hours
customthe resulting solution was reacted for one hour
customThen, the reaction mixture was reacted for further 4 hours
customAfter the reaction
customwas reacted for further 3 hours
filtrationthe resulting crystal was collected by filtration

Sources & evidence

ORD record: ord-01d7cb11d009480481c26673edfee863
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06201121B1

Reaction notes

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