Ethyl Acetoacetate → 2-(4-chlorobenzylthio)-7-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1073778Notes

Reaction equation

HRID 1073778 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[N:5][N:6]=1.[C:16](OCC)(=[O:21])[CH2:17][C:18]([CH3:20])=O>O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][S:7][C:4]2[S:3][C:2]3=[N:1][C:18]([CH3:20])=[CH:17][C:16](=[O:21])[N:6]3[N:5]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 3518875-(((4-Chlorophenyl)methyl)thio)-1,3,4-thiadiazol-2-amine

Product 1

HCID 156107832-(4-chlorobenzylthio)-7-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Twenty point two (20.2) g of the thus obtained 2-amino-5-(4-chlorobenzylthio)-1,3,4-thiadiazole and 12.2 g of ethyl acetoacetate were mixed with 24 g of polyphosphoric acid and the mixture was stirred at 130°~150° C. for 45 minutes. After cooling, water was added to the mixture, the mixture was extracted with chloroform, and the organic layer was washed with a sodium hydrogen carbonate aqueous solution and water respectively. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was recrystallized from ethanol and thus 21.3 g of 2-(4-chlorobenzylthio)-7-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained m.p. 138.5°~139.5° C. Yield 84%.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with chloroform
  3. washthe organic layer was washed with a sodium hydrogen carbonate aqueous solution and water respectively
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-e9100b7027764c3a9a37dc58e79caa5c
Source dataset
uspto-grants-1990_11
Patent number
US04971971

Reaction notes

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