HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Iodopentane → N-benzyl-N'-[3,5-bis(trifluoromethyl)benzoyl]-N-({4-[(pentyloxy)methyl]cyclohexyl}methyl)sulfamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Iodopentane | HCID 12335 | — |
| Reactant | 2,6-Di-tert-butylpyridine | HCID 68510 | — |
| Reactant | N-benzyl-N'-[3,5-bis(trifluoromethyl)benzoyl]-N-{[4-(hydroxymethyl)cyclohexyl]methyl}sulfamide | HCID 22574483 | — |
| Catalyst | Silver(I) trifluoromethanesulfonate | HCID 76223 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-benzyl-N'-[3,5-bis(trifluoromethyl)benzoyl]-N-({4-[(pentyloxy)methyl]cyclohexyl}methyl)sulfamide | HCID 22574478 | 73.9% |
Reaction Steps
Intermediate (4) (27.6 mg, 50 μmole, 1.0 eq) was dissolved in dichloromethane (250 μL), after which 2,6-di-t-butyl pyridine (36 μL, 160 μmole, 3.2 eq), silver triflate (38.5 mg, 150 μmole, 3.0 eq) and iodopentane (23 μL, 175 μmole, 3.5 eq) were added. After 45 minutes the reaction mixture was directly purified to give 23 mg of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 8.45 (s, 2H), 8.15 (s, 1H), 7.36 (d, 2H), 7.24 (t, 2H), 7.17 (t, 1H), 4.39 (s, 2H), 3.30 (water), 3.23 (t, 2H), 3.01 (d, 2H), 2.92 (d, 2H), 2.48 (DMSO), 1.61 (m, 2H), 1.54 (m, 2H), 1.41 (m, 2H), 1.34-1.19 (m, 6H), 0.82 (t, 3H), 0.62 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06852738B2 |
| Source dataset | uspto-grants-2005_02 |
| ORD ID | ord-a8255898e3c043f2be177310735149d0 |
| Source note | uspto-grants-2005_02 |