Water → HCID 19909379, compound

HRID 2073224Notes

Reaction equation

HRID 2073224 reaction equation
[NH2-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[Cl:10].Cl[CH2:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19].O>CCOCC>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24533Sodium amideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 76690(3,4-Dichlorophenyl)acetonitrile

Product 1

HCID 19909379HCID 19909379, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.9 g of sodium amide are added in small portions to a solution of 18.6 g of 3,4-dichlorophenylacetonitrile in 200 ml of anhydrous ether. The mixture is refluxed for 2 hours, 12.1 g of 3-chlorodimethylaminopropane are added and refluxing is continued for 2 and a half hours. The mixture is cooled, water is added and the organic phase is decanted. It is washed with water and extracted with 10% hydrochloric acid. The aqueous phase is then neutralized with 30% sodium hydroxide and extracted with ether and the solvent is evaporated off to give 17 g of the expected product.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. temperaturerefluxing
  3. customis continued for 2 and a half hours
  4. temperatureThe mixture is cooled
  5. customthe organic phase is decanted
  6. washIt is washed with water
  7. extractionextracted with 10% hydrochloric acid
  8. extractionextracted with ether
  9. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-61ab3737b55649ccaa9f93a9976848cc
Source dataset
uspto-grants-1990_04
Patent number
US04916156

Reaction notes

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