Hydrochloric Acid → 5-acetyloxy-N-benzylnaphthalene-2-sulfonamide
Reaction equation
C(N(CC)CC)C.[C:8]([O:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16]([S:22](Cl)(=[O:24])=[O:23])=[CH:17]2)(=[O:10])[CH3:9].[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>O1CCCC1>[C:8]([O:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16]([S:22]([NH:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:24])=[O:23])=[CH:17]2)(=[O:10])[CH3:9]Participants
6
Procedure
Triethylamine (50 μl, 0.36 mmol) and 5-(acetyloxy)naphthalene-2-sulfonyl chloride (84.9 mg, 0.30 mmol) were added to benzylamine (32.1 mg, 0.30 mmol) dissolved in tetrahydrofuran (3 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (eluent; n-hexane: ethyl acetate=2:1→1:1) to give the title compound as a light yellow white crystal (72.1 mg, 67.6%).
Workup
- extractionextracted with ethyl acetate
- washAfter the organic layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe residue obtained by evaporation of the solvent under reduced pressure
- customwas purified by column chromatography on silica gel (eluent; n-hexane: ethyl acetate=2:1→1:1)
Sources & evidence
- ORD record
- ord-98a0c763ac5b42f098ea16fb03200bca
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07598418B2
Reaction notes
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