Chlorobenzene → 2-hexylthio-7-hydroxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1073788Notes

Reaction equation

HRID 1073788 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N:5][N:6]=1.[C:14](OC1C(Cl)=CC(Cl)=CC=1Cl)(=[O:28])[CH2:15][C:16](OC1C(Cl)=CC(Cl)=CC=1Cl)=[O:17].ClC1C=CC=CC=1>CCCCCC>[CH2:8]([S:7][C:4]1[S:3][C:2]2=[N:1][C:14]([OH:28])=[CH:15][C:16](=[O:17])[N:6]2[N:5]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 1579472Sbb043676HCID 2783450Bis(2,4,6-trichlorophenyl) propanedioate

Product 1

HCID 1359674872-hexylthio-7-hydroxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 87%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 65.2 g of the thus obtained 2-amino-5-hexylthio-1,3,4-thiadiazole, 141.7 g of bis(2,4,6-trichlorophenyl) malonate and 240 ml of chlorobenzene was heated to 137°~140° C. and stirred for 1 hour. After cooling, hexane was added to the mixture, and the formed precipitate was separated by filtration, the residue was washed with hexane, and thus 74.7 g of 2-hexylthio-7-hydroxy-5H-1,3,4-thiadiazolo[3,2-a]-pyrimidin-5-one was obtained. m.p. 187°~192° C. Yield 87%.

Workup

  1. temperaturewas heated to 137°~140° C.
  2. temperatureAfter cooling
  3. customthe formed precipitate was separated by filtration
  4. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-408e243eebf443daba23e515cd58c641
Source dataset
uspto-grants-1990_11
Patent number
US04971971

Reaction notes

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