Chlorobenzene → 2-heptylthio-7-hydroxy-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1607540Notes

Reaction equation

HRID 1607540 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:5][N:6]=1.[CH3:15][CH:16]([C:29](OC1C(Cl)=CC(Cl)=CC=1Cl)=[O:30])[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:29]([OH:30])=[C:16]([CH3:15])[C:17](=[O:18])[N:6]2[N:5]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 5344581,3,4-Thiadiazole, 2-amino-5-(heptylthio)-HCID 12320374Bis(2,4,6-trichlorophenyl) methylpropanedioate

Product 1

HCID 1361201982-heptylthio-7-hydroxy-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 78%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 19.7 g of the thus obtained 2-amino-5-heptylthio-1,3,4-thiadiazole, 40.9 g of bis (2,4,6-trichlorophenyl) 2-methyl-malonate and 55 ml of chlorobenzene was stirred at 140°~144° C. for 45 minutes. After cooling, n-hexane was added thereto, the precipitate was collected by filtration. Further n-hexane was added to the filtrate, and the precipitate was collected. The collected precipitates were combined. The combinedprecipitate was washed with n-hexane and thus 21.2 g of 2-heptylthio-7-hydroxy-6-methyl-5H-1,3,4-thiadiazolo-[3,2-a]pyrimidin-5-one was obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was collected by filtration
  3. additionFurther n-hexane was added to the filtrate
  4. customthe precipitate was collected
  5. customThe collected precipitates
  6. washThe combinedprecipitate was washed with n-hexane

Sources & evidence

ORD record
ord-2ae8caf0855c42a392cf073a48a21c16
Source dataset
uspto-grants-1989_09
Patent number
US04866064

Reaction notes

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