Water → 1-(2-Mercapto-4-methoxyphenyl)-5-carboxypyrimidine-2,6-dione

HRID 224347Notes

Reaction equation

HRID 224347 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[N:7]=[C:8]([NH:10][CH:11]=[C:12]([C:18]([O:20]CC)=[O:19])[C:13](OCC)=[O:14])[S:9][C:5]=2[CH:4]=1.[OH-:25].[Na+].O>C(O)C>[SH:9][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:24]=[CH:23][C:6]=1[N:7]1[C:13](=[O:14])[C:12]([C:18]([OH:20])=[O:19])=[CH:11][NH:10][C:8]1=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 2798642Diethyl N-(6-methoxybenzthiazol-2-yl)-aminomethylenemalonate

Product 1

HCID 233328051-(2-Mercapto-4-methoxyphenyl)-5-carboxypyrimidine-2,6-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25 g. Diethyl N-(6-methoxybenzthiazol-2-yl)-aminomethylenemalonate are introduced into a solution of 36 g. sodium hydroxide, 360 ml. water and 120 ml. ethanol which has been heated to 70° C. and the reaction mixture is heated under reflux for 30 minutes. A part of the ethanol is then removed in vacuo, filtered and, after cooling, the filtrate is acidified with 2 N hydrochloric acid. 1-(2-Mercapto-4-methoxyphenyl)-5-carboxypyrimidine-2,6-dione is obtained in a yield of 14.7 g. (70% of theory). According to the melting point and the IR, UV and NMR spectra, the product is identical with the compound prepared according to Variant I.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 30 minutes
  3. customA part of the ethanol is then removed in vacuo
  4. filtrationfiltered
  5. temperatureafter cooling

Sources & evidence

ORD record
ord-1914d707feea48e1ad61cb1946823bb7
Source dataset
uspto-grants-1980_11
Patent number
US04232024

Reaction notes

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