HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-(4-tert-Butylphenyl)-1,3,4-thiadiazol-2-amine → 2-(4-tert-butylphenyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-(4-tert-Butylphenyl)-1,3,4-thiadiazol-2-amine | HCID 811160 | — |
| Reactant | 3-Oxo-3-(2,4,6-trichlorophenoxy)propanoate | HCID 19868146 | — |
| Solvent | 1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) | HCID 24670 | — |
| Product | 2-(4-tert-butylphenyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one | HCID 135802450 | 96.6% |
Reaction Steps
A mixture of 9.3 g of 2-amino-5-(4-tert-butylphenyl)-1,3,4-thiadiazole, 20 g of 2,4,6-trichlorophenyl malonate and 50 ml of Dowtherm A was heated at a temperature of 120° to 130° C. for 2 hours. After allowing the mixture to cool, the precipitate was separated by filtration, washed successively with isopropanol and diethyl ether to obtain 11.6 g of 2-(4-tert-butylphenyl)-7-hydroxy-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one as a colorless, crystalline powder having a melting point of 265° to 268° C. (decomposition).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04652646 |
| Source dataset | uspto-grants-1987_03 |
| ORD ID | ord-eff97c3f4dcd41f99dd3a61bda38d05a |
| Source note | uspto-grants-1987_03 |