Thionyl Chloride → 3-{Benzyl-[2-(2-bromophenyl)-2-chloroethyl]amino}propanenitrile

HRID 1859050Notes

Reaction equation

HRID 1859050 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]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 221232233-{Benzyl-[2-(2-bromophenyl)-2-hydroxyethyl]amino}propanenitrile

Product 1

HCID 221232083-{Benzyl-[2-(2-bromophenyl)-2-chloroethyl]amino}propanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customthe reaction mixture is evaporated to dryness
  2. filtrationfiltered
  3. customAfter separating off
  4. customdrying
  5. customevaporating under reduced pressure, 90.2 g of expected product
  6. customare obtained

Sources & evidence

ORD record
ord-9b4761b7cd034018a848e6fc2d082d0d
Source dataset
uspto-grants-2000_11
Patent number
US06153640

Reaction notes

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