Reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH2:18])[CH3:14].[CH2:21]([NH:28][CH2:29][CH2:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:33])=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH:18][C:1](=[O:2])[N:28]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:29][CH2:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:33])=[O:32])[CH3:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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).
Workup
- temperaturethe mixture was refluxed for 16 hr
- customThe solvent was removed in vacuo
- customthe residue was partitioned between methylene chloride and water
- dry with materialThe methylene chloride solution was dried over magnesium sulfate
- customthe solvent was removed in vacuo
- customto give an oil
Sources & evidence
- ORD record
- ord-ba4345f5b99a41f9b978c196be6e203c
- Source dataset
- uspto-grants-1986_07
- Patent number
- US04597902
Linked notes
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