Dimethylformamide → HCID 57530581, compound
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][NH2:8].CCN(C(C)C)C(C)C.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20].C(Cl)Cl.CN([CH:32]=[O:33])C>>[Si:22]([O:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][NH:8][C:32]1=[O:33])([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23]Participants
6
Conditions
- Temperature
- 50 °C
Procedure
N-(3-hydroxypropyl)ethylenediamine (19.9 g, 168 mmol), DIPEA (87 mL, 504 mmol, 3.0 eq) were dissolved in 500 mL DMF, followed by the addition of 1,1-carbonyldiimidazole (27.3 g, 168 mmol, 1.0 eq). The reaction was allowed to stir at 50° C. overnight. After overnight, the reaction was cooled to room temperature and TBSCl (25.2 g, 168 mmol, 1.0 eq) was added. The mixture was allowed to stir at room temperature for 3 hours. The reaction was then condensed in vacuo at 40° C. and the obtained residue was then taken into DCM (500 mL). The organic phase was washed with water (2×500 mL) and then with brine (500 mL), dried over MgSO4, filtered and concentrated to afford the title compound as a light yellow solid (42.8 g) in 98% yield.
Workup
- waitAfter overnight
- temperaturethe reaction was cooled to room temperature
- stirringto stir at room temperature for 3 hours
- customcondensed in vacuo at 40° C.
- washThe organic phase was washed with water (2×500 mL)
- dry with materialwith brine (500 mL), dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e302fa928fd1409d8105806e8e709910
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07479562B2
Reaction notes
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