Acrylonitrile → HCID 18978058, compound

HRID 2392990Notes

Reaction equation

HRID 2392990 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[C:5]([O:9][C:10]([N:12]([CH3:17])[CH2:13][CH2:14][NH:15][CH3:16])=[O:11])([CH3:8])([CH3:7])[CH3:6]>>[C:5]([O:9][C:10]([N:12]([CH3:17])[CH2:13][CH2:14][N:15]([CH2:3][CH2:2][C:1]#[N:4])[CH3:16])=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 14403871tert-Butyl methyl(2-(methylamino)ethyl)carbamate

Product 1

HCID 18978058HCID 18978058, compoundYield 79.7%

Conditions

Temperature
60 °C

Procedure

530 mg of acrylonitrile were slowly added to 1.88 g of N-(tert-butoxycarbonyl)-N,N'-dimethyl-ethylenediamine, while cooling with ice. The mixture was stirred at 0° C. for 1 hour, at RT for 14 hours and at 60° C. for 2 hours. The volatile constituents were removed in vacuo and the residue was purified by chromatography over silica gel (EA:MeOH 9:1). 1.92 g of product were obtained. MS(Cl): 242 (M+H)⊕, 186, 142

Workup

  1. temperaturewhile cooling with ice
  2. customThe volatile constituents were removed in vacuo
  3. customthe residue was purified by chromatography over silica gel (EA:MeOH 9:1)

Sources & evidence

ORD record
ord-9d65133a8cd34c2e9f1a6336213ed633
Source dataset
uspto-grants-1998_09
Patent number
US05804559

Reaction notes

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