Triethylamine → HCID 23293447, compound
Reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7].Cl[CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].C(N(CC)CC)C>CN(C)C=O>[OH:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=1[O:4][CH2:3][CH2:2][OH:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
6 g (39.17 mmol) 2-(2-hydroxyethoxy)aniline A3, 5 ml (5.85 g, 47 mmol) 2-(2-chloroethoxy)ethanol and 8.19 ml (5.95 g, 58.75 mmol) triethylamine were dissolved in 20 ml dimethylformamide and stirred for 4 days at 90° C. After cooling, the solution was filtered, the precipitate washed with dichloromethane and the filtrate concentrated in vacuo. The residue was taken up in chloroform and washed twice with a small quantity of water. The chloroform solution was then dried over sodium sulfate and concentrated. The viscous crude product was purified by column chromatography on silica gel 60 with toluene/acetone 1:2 as the mobile phase. 5 g of brown, viscous oil were obtained; yield 53%.
Workup
- temperatureAfter cooling
- filtrationthe solution was filtered
- washthe precipitate washed with dichloromethane
- concentrationthe filtrate concentrated in vacuo
- washwashed twice with a small quantity of water
- dry with materialThe chloroform solution was then dried over sodium sulfate
- concentrationconcentrated
- customThe viscous crude product was purified by column chromatography on silica gel 60 with toluene/acetone 1:2 as the mobile phase
- custom5 g of brown, viscous oil were obtained
Sources & evidence
- ORD record
- ord-3150d7c83b8d4c18ac8a366bfd0dd166
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124135
Reaction notes
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