反応 #48232

反応方程式

EtOAc n-hexane

vanillin

N,N-dimethylsulfamoyl chloride

→

4-(N,N-Dimethylsulfamoyl)-3-methoxybenzaldehyde

溶媒

n-hexane

EtOAc

N,N-dimethylcyclohexylamine

反応条件

後処理

1. 1
   その他transferred to a separating funnel
2. 2
   洗浄The organic layer was washed with water (2×200 mL), 6M HCl (aq.) (200 mL), brine (2×200 mL)
3. 3
   乾燥dried (Na2SO4)
4. 4
   ろ過filtered
5. 5
   濃縮Concentration in vacuo of the combined filtrates
6. 6
   その他gave a golden-yellow oil which
7. 7
   ろ過filtered
8. 8
   その他air-dried
9. 9
   その他to give OBS02011 as yellow plates (6.92 g, 89%)

実験手順

To a solution of vanillin (4.56 g, 30 mmol) in N,N-dimethylcyclohexylamine (30 mL) at 80-90° C., was added N,N-dimethylsulfamoyl chloride (3.79 mL, 35.27 mmol). The mixture was stirred at this temperature for 4 h, transferred to a separating funnel and diluted with EtOAc (100 mL). The organic layer was washed with water (2×200 mL), 6M HCl (aq.) (200 mL), brine (2×200 mL), dried (Na2SO4) and filtered. Concentration in vacuo of the combined filtrates gave a golden-yellow oil which solidified on standing. The product was stirred in n-hexane, filtered and air-dried to give OBS02011 as yellow plates (6.92 g, 89%). TLC [SiO2, EtOAc-n-hexane (1:1)] Rf=0.65; 1H-NMR (270 MHz, CDCl3)=2.98 (6H, s), 3.93 (3H, s), 7.44 (1H, d, J=1.6), 7.48 (1H, dd, J=1.6, 8.1), 7.53 (1H, d, J=8.1), 9.92 (1H, s).

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