Chlorobenzene → 2-(Benzylthio)-7-hydroxy-5H-1,3,4-thiadiazolo(3,2-a)pyrimidin-5-one

HRID 703834

Reaction equation

HRID 703834 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:15](OC1C(Cl)=CC(Cl)=CC=1Cl)(=[O:29])[CH2:16][C:17](OC1C(Cl)=CC(Cl)=CC=1Cl)=[O:18].ClC1C=CC=CC=1>CCCCCC>[CH2:8]([S:7][C:4]1[S:3][C:2]2=[N:1][C:15]([OH:29])=[CH:16][C:17](=[O:18])[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 7964ChlorobenzeneHCID 992851,3,4-Thiadiazol-2-amine, 5-((phenylmethyl)thio)-HCID 2783450Bis(2,4,6-trichlorophenyl) propanedioate

Product 1

HCID 1355943712-(Benzylthio)-7-hydroxy-5H-1,3,4-thiadiazolo(3,2-a)pyrimidin-5-oneYield 98%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 44.7 g of 2-amino-5-benzylthio-1,3,4-thiadiazole, 98.1 g of bis(2,4,6-trichlorophenyl) malonate and 140 ml of chlorobenzene was heated to 130°-140° C. and stirred for 20 minutes. After cooling, hexane was added to the mixture, and the formed precipitate was separated by filtration. The solid was washed with hexane and thus 57.1 g of 2-benzylthio-7-hydroxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. Yield 98%.

Workup

  1. temperaturewas heated to 130°-140° C.
  2. temperatureAfter cooling
  3. customthe formed precipitate was separated by filtration
  4. washThe solid was washed with hexane

Sources & evidence

ORD record
ord-1f7a92d2e44a421793691518bc4b4866
Source dataset
uspto-grants-1991_01
Patent number
US04985432

Linked notes

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