Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Acetyl-3-hydroxy-2-propylbenzyl chloride | HCID 13781022 | — |
| Reactant | HCID 178471526 | HCID 178471526 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Methyl Ethyl Ketone | HCID 6569 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 14839458 | HCID 14839458 | 83.8% |
Reaction Steps
To a mixture of 0.30 g of 4-acetyl-3-hydroxy-2-propylbenzyl chloride, 0.39 g of ethyl 5-[(5-mercapto-1,3,4-thiadiazol-2-yl)thio]valerate, 0.20 g of anhydrous potassium carbonate and 4 ml of methyl ethyl ketone were added catalytic amounts of potassium iodide and tetra-n-butylammonium bromide followed by stirring at 60° C. for 3 hours. The reaction mixture was diluted with ethyl acetate and insoluble matters were filtered off. The filtrate was washed with an aqueous sodium hydroxide solution and dried over anhydrous magnesium sulfate. The solvent was then distilled off. The residue was applied to silica gel column chromatography. Elution with a mixture of hexane-ethyl acetate (5:1) gave 0.52 g of oily ethyl 5-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thio]valerate
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04933348 |
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| Source dataset | uspto-grants-1990_06 |
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| ORD ID | ord-a376af5463aa4fa0b56c4429af273807 |
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| Source note | uspto-grants-1990_06 |
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