Chloride → N,N-bis-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-chloro-acetamide
Reaction equation
[Cl-].[C:2](=[O:5])([O-])[O-].[K+].[K+].[C:8]([Si:12]([CH3:28])([CH3:27])[O:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][O:19][Si:20]([CH3:26])([CH3:25])[C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:11])([CH3:10])[CH3:9].[Cl:29][CH2:30]Cl>>[C:21]([Si:20]([CH3:25])([CH3:26])[O:19][CH2:18][CH2:17][N:16]([CH2:15][CH2:14][O:13][Si:12]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:28])[CH3:27])[C:2](=[O:5])[CH2:30][Cl:29])([CH3:22])([CH3:24])[CH3:23]Participants
5
Procedure
Choloroacetyl chloride (1.1 g, 9.55 mmol) and potassium carbonate (2.638 g, 19.09 mmol) were dissolved in dry dichloromethane (80 mL) and cooled in an ice salt bath. To this was added bis-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]amine (3.353 g, 9.545 mmol) in dry dichloromethane (10 mL) over 10 minutes. The reaction mixture was stirred in an ice bath for 2 hours. The mixture was filtered and washed with dichloromethane, then washed with 1.5 N aqueous potassium hydrogen sulfate (2×100 mL) and brine (100 mL). The aqueous layers were back extracted with dichloromethane (2×100 mL), dried over sodium sulfate, filtered and concentrated in vacuo to give N,N-bis-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-chloro-acetamide (3.8 g, 87.4%).
Workup
- temperaturecooled in an ice salt bath
- filtrationThe mixture was filtered
- washwashed with dichloromethane
- washwashed with 1.5 N aqueous potassium hydrogen sulfate (2×100 mL) and brine (100 mL)
- extractionThe aqueous layers were back extracted with dichloromethane (2×100 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-57e2da6e7eae4216b7fe77513b0c0a7a
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557221B2
Reaction notes
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