反応 #2358568

反応方程式

N-(3,4-dimethoxyphenylsulfonyl)-N-hexyl-3,4-dimethoxybenzenesulfonamide

→

N-(3,4-dihydroxyphenylsulfonyl)-N-hexyl-3,4-dihydroxybenzenesulfonamide

収率 65.0%

溶媒

CH2Cl2

boron tribromide

反応条件

後処理

1. 1
   その他Upon quenching with a few drops of water
2. 2
   その他a precipitate formed
3. 3
   ろ過was filtered
4. 4
   その他The solid was triturated with ethyl acetate
5. 5
   その他the filtrate was evaporated

実験手順

To a 0° C. solution of N-(3,4-dimethoxyphenylsulfonyl)-N-hexyl-3,4-dimethoxybenzenesulfonamide (0.080 g, 0.181 mmol) in 1.81 mL of CH2Cl2, boron tribromide (1.81 mL, 1M in CH2Cl2) was added dropwise under a nitrogen atmosphere. The resulting solution was allowed to stir overnight and warm to room temperature. Upon quenching with a few drops of water, a precipitate formed and was filtered. The solid was triturated with ethyl acetate and the filtrate was evaporated, affording 0.046 g (65%) of N-(3,4-dihydroxyphenylsulfonyl)-N-hexyl-3,4-dihydroxybenzenesulfonamide as white solid. 1H NMR (acetone-d6, 400 MHz) δ 7.43 (d, J=2.3 Hz, 2H), 7.34 (dd, J=2.3, 8.2 Hz, 2H), 6.97 (d, J=8.2 Hz, 2H), 3.58 (m, 2H), 1.61 (m, 2H), 1.22 (m, 6H), 0.81 (t, J=6.9 Hz, 3H); 13C NMR (acetone-d6, 100 MHz) δ 150.61, 145.17, 131.03, 121.33, 115.07, 115.06, 49.01, 31.10, 26.05, 22.30, 13.42; HRMS, ES calcd. for C18H23NO8S2Na[M+Na]+468.0763, found: 468.0755.

出典