Triethylamine → HCID 86635468, compound

HRID 2261793Notes

Reaction equation

HRID 2261793 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:26])[CH2:23][CH2:24][OH:25])=[C:18]([CH3:27])[CH:17]=2)=[C:12]([CH:28]([CH3:30])[CH3:29])[CH:11]=[N:10]1.C(N(CC)CC)C.[N+:38]([C:41]1[CH:42]=[C:43]([S:47](Cl)(=[O:49])=[O:48])[CH:44]=[CH:45][CH:46]=1)([O-:40])=[O:39]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:26])[CH2:23][CH2:24][O:25][S:47]([C:43]3[CH:44]=[CH:45][CH:46]=[C:41]([N+:38]([O-:40])=[O:39])[CH:42]=3)(=[O:48])=[O:49])=[C:18]([CH3:27])[CH:17]=2)=[C:12]([CH:28]([CH3:30])[CH3:29])[CH:11]=[N:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 86635467HCID 86635467, compound

Product 1

HCID 86635468HCID 86635468, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+/−)-3-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-butan-1-ol (0.245 g, 0.548 mmol) in dichloromethane (10 mL) is added triethylamine (0.15 mL, 1.09 mmol). After 10 minutes, m-nitrobenzene sulfonyl chloride (0.243 g, 1.09 mmol) is added. The reaction is stirred at room temperature for 4 hours and the reaction mixture is concentrated under reduced pressure. The residue is dissolved in ethyl acetate and is washed with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound. 1H NMR (CDCl3) δ 1.1 (d, 3H), 1.28 (d, 6H), 1.62 (s, 2H), 1.85-1.95 (m, 2H), 2.17 (s, 3H), 2.91-3.039 (m, 2H), 3.85-3.95 (m, 1H), 4.04-4.12 (m, 2H), 4.74 (s, 2H), 6.45 (d, 1H), 6.51 (dd, 1H), 6.86 (d, 1H), 7.26 (t, 1H), 7.38 (d, 2H), 7.65 (t, 3H), 8.1 (d, 1H), 8.39 (d, 1H), 8.63 (s, 1H);

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washis washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-78d2efb275754cfd9009f253b487b93e
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…