O-Xylene → 2-benzylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 703839Notes

Reaction equation

HRID 703839 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][N:6]=1.C([O:17][CH:18]=[CH:19][C:20](OCC)=O)C.C1(C)C(C)=CC=CC=1>O>[CH2:8]([S:7][C:4]1[S:3][C:2]2=[N:1][CH:20]=[CH:19][C:18](=[O:17])[N:6]2[N:5]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 992851,3,4-Thiadiazol-2-amine, 5-((phenylmethyl)thio)-HCID 221780Ethyl 3-ethoxy-2-propenoate

Product 1

HCID 142544292-benzylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Fifteen point five (15.5) grams of 2-amino-5-benzylthio-1,3,4-thiadiazole, 10 g of ethyl 3-ethoxypropenoate, 15 g of polyphosphoric acid and 15 ml of xylene were mixed and vigorously stirred for 30 minutes. After the reaction was finished, the reaction mixture was cooled. Water was added to the reaction mixture and the mixture was extracted with toluene. The organic layer was washed with an aqueous sodium hydrogen carbonate solution and water respectively and dried over anhydrous sodium sulfate. The solvent was distilled off, the residue was recrystallized from an ethanol/hexane mixture, and thus 10.3 g of 2-benzylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. Yield 54%.

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionthe mixture was extracted with toluene
  3. washThe organic layer was washed with an aqueous sodium hydrogen carbonate solution and water respectively
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was recrystallized from an ethanol/hexane mixture

Sources & evidence

ORD record
ord-782d3eda1be948168e68848e8081f808
Source dataset
uspto-grants-1991_01
Patent number
US04985432

Reaction notes

Loading…