Thionyl Chloride → 3-{Benzyl-[2-(2-bromophenyl)-2-chloroethyl]amino}propanenitrile
Reaction equation
[CH2:1]([N:8]([CH2:13][CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Br:22])O)[CH2:9][CH2:10][C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>C(Cl)Cl>[CH2:1]([N:8]([CH2:13][CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Br:22])[Cl:25])[CH2:9][CH2:10][C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
The 94 g of product obtained in Step 2 are dissolved in 400 ml of methylene chloride. At ambient temperature, within a period of 1 hour, 90.5 ml of thionyl chloride are poured in dropwise. After stirring for 12 hours at ambient temperature, the reaction mixture is evaporated to dryness and then taken up in ether and filtered. The solid is taken up in 500 ml of 10% aqueous sodium carbonate solution and 1 litre of methylene chloride. After separating off, drying and evaporating under reduced pressure, 90.2 g of expected product are obtained.