Chloroform → 2-benzylthio-6-methoxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 703833

Reaction equation

HRID 703833 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.[OH:15][CH:16]=[C:17]([O:24][CH3:25])[C:18](OCCC)=O.C(Cl)(Cl)Cl>O>[CH2:8]([S:7][C:4]1[S:3][C:2]2=[N:1][CH:18]=[C:17]([O:24][CH3:25])[C:16](=[O:15])[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 6212ChloroformHCID 992851,3,4-Thiadiazol-2-amine, 5-((phenylmethyl)thio)-HCID 71336589Propyl 3-hydroxy-2-methoxyprop-2-enoate

Product 1

HCID 142544232-benzylthio-6-methoxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Four (4) grams of the thus obtained 2-amino-5-benzylthio-1,3,4-thiadiazole, 3.2 g of propyl 3-hydroxy-2-methoxy-propenoate and 11 g of polyphosphoric acid were heated to 135° C. and stirred for 20 minutes. After cooling, chloroform and water were added thereto, extraction was carried out. The organic layer was washed with an aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was washed with an ethanol/hexane mixture and 5.1 g of 2-benzylthio-6-methoxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. Yield 93%. The compound was recrystallized from ethanol. m.p. 145°-147° C.

Workup

  1. temperatureAfter cooling
  2. extractionextraction
  3. washThe organic layer was washed with an aqueous sodium hydrogen carbonate solution and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. washthe residue was washed with an ethanol/hexane mixture

Sources & evidence

ORD record
ord-ca8a64f9a8e3465db27d2aec6e5c920f
Source dataset
uspto-grants-1991_01
Patent number
US04985432

Linked notes

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