HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 5-(4-Chlorophenyl)-4-cyclopropyl-2-({4-[2-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-yl}-methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | 1-Ethynyl-2-(trifluoromethyl)benzene | HCID 4100856 | — |
| Reactant | 2-(Chloromethyl)-5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one | HCID 67411647 | — |
| Catalyst | Cupric acetate monohydrate | HCID 165397 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 5-(4-Chlorophenyl)-4-cyclopropyl-2-({4-[2-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-yl}-methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one | HCID 69940376 | — |
Reaction Steps
60 mg (0.21 mmol) of the compound from Example 122A were dissolved in 2 ml of acetonitrile, 14 mg (0.21 mmol) of sodium azide were added and the mixture was stirred at RT for 1 h. 0.4 mg (0.002 mmol) of copper(II) acetate monohydrate and 43 mg (0.25 mmol) of 1-ethynyl-2-(trifluoro-methyl)benzene were then added. The resulting mixture was stirred at RT for 20 h. For work-up, 10 ml of ethyl acetate were added and the mixture was washed twice with in each case 5 ml of water. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 48 mg (45% of theory) of the target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09187466B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-65855bc6aedf41f88f4a5b2e21ce0b19 |
| Source note | uspto-grants-2015_11 |