HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 4-((3,4-Dichlorophenoxy)methyl)-2,5-difluoro-N-(methylsulfonyl)benzamide Diethylamine salt
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | 4-((3,4-Dichlorophenoxy)methyl)-2,5-difluorobenzamide | HCID 66667234 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-((3,4-Dichlorophenoxy)methyl)-2,5-difluoro-N-(methylsulfonyl)benzamide Diethylamine salt | HCID 86682555 | — |
Reaction Steps
To 4-((3,4-dichlorophenoxy)methyl)-2,5-difluorobenzamide (Preparation 24, 60 mg, 0.18 mmol) in THF (2 mL) was added a THF solution of lithium hexamethyldisilazide (1 M, 0.362 mL, 0.362 mmol) over 2 minutes. After stirring for 15-20 minutes, methanesulphonyl chloride (0.028 mL, 0.362 mmol) was added and the solution was stirred for 18 hours at room temperature. The reaction mixture was then diluted with EtOAc and washed twice with water. The organic layer was dried over sodium sulphate and evaporated to yield a yellow oil (65 mg), which was purified by preparative HPLC to yield the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09096500B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-a7e8aa6f166f4cfabc63cf03e31ef5aa |
| Source note | uspto-grants-2015_08 |