Methanol → HCID 43084538, compound

HRID 1666699Notes

Reaction equation

HRID 1666699 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[Cl:12])[CH2:6]CN.C([N:15]([CH2:18][CH3:19])[CH2:16]C)C.CO.[C:22](#[N:25])C=C>C(OCC)(=O)C>[Cl:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[Cl:12])[CH2:6][N:15]([CH3:16])[CH2:18][CH2:19][C:22]#[N:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 7855AcrylonitrileHCID 8471TriethylamineHCID 217957Phenethylamine, 3,4-dichloro-, hydrochloride

Product 1

HCID 43084538HCID 43084538, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

From 20 g (88 mmol) N-(3,4-Dichlorobenzyl)methylamine hydrogen chloride salt the base is liberated by the addition of 12.6 ml (90 mmol) triethylamine in 100 ml ethyl acetate solution. The resulting 16.5 g base is dissolved in 170 ml abs. methanol, the solution is cooled to below 0° C. and 5.7 ml (87 mmol) acrylonitrile is added to it. The reaction mixture is stirred at 0° C. for 30 minutes, allowed to reach room temperature, stirred for 30 hours and evaporated to obtain 20 g of the title compound in the form of an oil. LC/MS[MH+]=243 (C11H12Cl2N2 243.14).

Workup

  1. customto reach room temperature
  2. stirringstirred for 30 hours
  3. customevaporated

Sources & evidence

ORD record
ord-73fae92b356c4b9d832cbd8adc207dd4
Source dataset
uspto-grants-2011_10
Patent number
US08044078B2

Reaction notes

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