Sodium Hydroxide → 1-Ethylquinazoline-2,4(1H,3H)-dione

HRID 611474Notes

Reaction equation

HRID 611474 reaction equation
[CH2:1]([NH:3][C:4]1[C:5](=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:6]([OH:8])=O)[CH3:2].[O-:13][C:14]#[N:15].[Na+].[OH-].[Na+]>C(O)(=O)C>[CH2:1]([N:3]1[C:4]2[C:5](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:8])[NH:15][C:14]1=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66642Benzoic acid, 2-(ethylamino)-HCID 517096Sodium Cyanate

Product 1

HCID 8253101-Ethylquinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Am. Chem. Soc. (1933), pages 2113-2116 describes the reaction of N-ethylanthranilic acid with sodium cyanate and acetic acid and subsequent addition of sodium hydroxide to give 1,2,3,4-tetrahydro-1-ethyl-2,4-dioxoquinazoline. However, disadvantages of this process are the low space yield, because of the dilute reaction solution, and the very high excess of sodium hydroxide.

Sources & evidence

ORD record
ord-b8d99ac57f3c45f2a2fa37b559ad9fca
Source dataset
uspto-grants-1999_12
Patent number
US06001831

Reaction notes

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