Reaktion #1934

Reaktionsgleichung

3,4-dichlorobenzaldehyde

cyanotrimethylsilane

2-(methylamino)ethanol

→

expected product

2-(3,4-Dichlorophenyl)-2-[N-(2-hydroxyethyl)-N-methylamino]acetonitrile

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis cooled in an ice bath
2. 2
   Temperaturthe reaction mixture is heated at 60° C. for 2 hours
3. 3
   workup.WAITAfter one night at RT
4. 4
   Einengenit is concentrated under vacuum
5. 5
   Extraktionthe residue is extracted with ether
6. 6
   Waschenthe organic phase is washed with water
7. 7
   Trocknendried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   workup.ADDITIONThe filtrate is acidified to pH 1 by the addition of a saturated solution of hydrochloric acid in ether, acetone
10. 10
    workup.ADDITIONis added
11. 11
    workup.STIRRINGthe mixture is stirred until crystallization

Vorschrift

A mixture of 10 g of 3,4-dichlorobenzaldehyde and 9.5 ml of cyanotrimethylsilane is cooled in an ice bath, 0.01 g of zinc iodide is added and the mixture is stirred for 15 minutes at RT. A solution of 4.5 g of 2-(methylamino)ethanol in 50 ml of MeOH is then added and the reaction mixture is heated at 60° C. for 2 hours. After one night at RT, it is concentrated under vacuum, the residue is extracted with ether and the organic phase is washed with water, dried over MgSO4 and filtered. The filtrate is acidified to pH 1 by the addition of a saturated solution of hydrochloric acid in ether, acetone is added and the mixture is stirred until crystallization occurs. This gives 15 g of the expected product after wringing of the crystals formed. M.p.=130° C.

Quelle