Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrazine | HCID 9321 | — |
| Reactant | 1,1'-Thiocarbonyldiimidazole | HCID 80264 | — |
| Reactant | 2-(3-Azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole | HCID 86604831 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86608777 | HCID 86608777 | 20% |
Reaction Steps
2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole (577 mg, 1.61 mmol) was dissolved in 8 mL THF, followed by addition of thio-carbonyldiimidazole (458 mg, 2.57 mmol), and heated to reflux for 1 hour. The reaction mixture was cooled to 23° C., and hydrazine (257 mg, 8.03 mmol) was added. The reaction mixture was stirred for 12 hours. The crude reaction mixture was then concentrated and purified by flash column chromatography, eluting with 4:1 (hexanes/ethyl acetate), to afford the desired product (135 mg, 20%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09221841B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-fe01f58ae9534f329435839c8833dc1a |
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| Source note | uspto-grants-2015_12 |
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