HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → N-(5-bromo-pyridin-2-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | (5-Bromopyridin-2-yl)methanol | HCID 5200169 | — |
| Reactant | 2-chloro-N-isobutyl-benzenesulfonamide | HCID 8469376 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(5-bromo-pyridin-2-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide | HCID 67439287 | 57.1% |
Reaction Steps
To a stirred solution of 2-chloro-N-isobutyl-benzenesulfonamide (example 42, step 1, 110 mg) in tetrahydrofuran (2.5 mL) were added (5-bromo-pyridin-2-yl)-methanol (CAS [88139-91-7], 92 mg), triphenylphosphine (129 mg) and diethyl azodicarboxylate (88 mg). The mixture was stirred for 48 h at r.t. The solvent was evaporated under reduced pressure and the product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 0:1) to give N-(5-bromo-pyridin-2-ylmethyl)-2-chloro-N-isobutyl-benzenesulfonamide (106 mg) as a colorless oil. MS: 417.2 ([M+H]+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08039493B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-09facf3a089e4d3d98cf7ccecd01739e |
| Source note | uspto-grants-2011_10 |