Sodium hydride → HCID 18933661, compound
Reaction equation
[CH2:1]([N:8]([CH3:12])[CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[Cl:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22](F)[C:19]=1[CH:20]=[O:21]>CN(C=O)C>[CH2:1]([N:8]([CH2:9][CH2:10][O:11][C:22]1[CH:23]=[CH:24][CH:25]=[C:18]([Cl:17])[C:19]=1[CH:20]=[O:21])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
A solution of N-benzyl-N-methylethanolamine (13.4 g) in dry DMF (30 ml) was added dropwise with stirring to a suspension of sodium hydride (4.75 g, 60% dispersion in mineral oil) in DMF (60 ml) at ambient temperature under nitrogen over 20 minutes. The mixture was stirred and heated at 50° C. for 1 hour until the evolution of hydrogen ceased. The mixture was cooled at ambient temperature and a solution of 2-chloro-6-fluorobenzaldehyde (15.8 g) in DMF (15 ml) was added over 30 minutes. The mixture was heated at 70° C. for 2 hours and then cooled and poured onto ice/water (1 l). The mixture was extracted with ethyl acetate. The combined ethyl acetate extracts were washed with 2M sodium hydroxide solution and then brine, dried and evaporated to give 2-[2-(N-benzyl-N-methylamino)ethoxy]-6-chlorobenzaldehyde as an oil.
Workup
- temperatureThe mixture was heated at 70° C. for 2 hours
- temperaturecooled
- additionpoured onto ice/water (1 l)
- extractionThe mixture was extracted with ethyl acetate
- washThe combined ethyl acetate extracts were washed with 2M sodium hydroxide solution
- dry with materialbrine, dried
- customevaporated
Sources & evidence
- ORD record
- ord-e999033143d845e09817741ec7f8b858
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05736568
Reaction notes
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