Hydrochloric Acid → alpha-(Dimethylamino)-3-phenoxybenzeneacetonitrile

HRID 904900Notes

Reaction equation

HRID 904900 reaction equation
[CH3:1][NH:2][CH3:3].Cl.[O:5]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C-:20]#[N:21].[Na+].CCCCCCCCCC1C=CC(O)=CC=1.C1OC1>O.ClCCl>[CH3:1][N:2]([CH3:3])[CH:15]([C:14]1[CH:17]=[CH:18][CH:19]=[C:12]([O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:13]=1)[C:20]#[N:21]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 17524-NonylphenolHCID 6354Ethylene OxideHCID 8929Sodium CyanideHCID 382843-Phenoxybenzaldehyde

Product 1

HCID 13565187alpha-(Dimethylamino)-3-phenoxybenzeneacetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of dimethylamine in water (5 ml of a 26% w/v solution; 30 mmole) and water (5 ml) was neutralised with concentrated hydrochloric acid. 3-Phenoxybenzaldehyde (3.96 g, 20 mmole) was added to the stirred solution followed by sodium cyanide (1.5 g, 30 mmole) and "Teric" N8 (5 drops of a 10% aqueous solution; "Teric" is an ICI Australia Limited Trade Mark and "Teric" N8 is the product of condensation of nonylphenol and ethylene oxide in the mole ratio of 1:8). The mixture was stirred vigorously for a period of 1 hour and then dichloromethane (50 ml) was added. The organic phase was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give the title compound as a pale yellow oil (5.2 g). Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 2.3 (6H, s, N(CH3)2); 4.8 (1H, s, CH); 6.9-7.6 (9H, m, aromatic protons).

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-8e83966361074dd3880c32b4b0b637fb
Source dataset
uspto-grants-1983_12
Patent number
US04420614

Reaction notes

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