反応 #832374

反応方程式

1,1'-carbonyldiimidazole

N,N-diethylethylenediamine

N-benzyl-2-phenylsulfonylethanamine

→

oil

収率 70.0%

N'-[2-(Diethylamino)ethyl]-N-(phenylmethyl)-N-[2-(phenylsulfonyl)ethyl]urea

収率 70.0%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度the mixture was refluxed for 16 hr
2. 2
   その他The solvent was removed in vacuo
3. 3
   その他the residue was partitioned between methylene chloride and water
4. 4
   乾燥The methylene chloride solution was dried over magnesium sulfate
5. 5
   その他the solvent was removed in vacuo
6. 6
   その他to give an oil

実験手順

A mixture of 3.89 (0.024 mole) of 1,1'-carbonyldiimidazole and 2.55 g (0.022 mole) of N,N-diethylethylenediamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 5.70 g (0.0183 mole) of N-benzyl-2-phenylsulfonylethanamine in 50 ml of tetrahydrofuran was added, and the mixture was refluxed for 16 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and water. The methylene chloride solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (methanol) gave 5.35 g (69.98%) of oil: 1H NMR (CDCl3) δ7.45-8.00 (m, 5, C6H5SO2), 7.05-7.40 (m, 5, C6H5CH2), 5.65 (br s, 1, NH), 4.2 (s, C6H5CH2), 3.0-3.84 (m, 6, SO2CH2CH2 and NHCH2) 2.2-2.65 (m, 6, CH2N(CH2CH3)2), 0.90 (t, 6, CH3).

出典