Methoxyacetonitrile → 3,3-Bis(dimethylamino)-2-methoxypropanenitrile

HRID 1484671Notes

Reaction equation

HRID 1484671 reaction equation
C(O[CH:6]([N:10]([CH3:12])[CH3:11])[N:7]([CH3:9])[CH3:8])(C)(C)C.[CH3:13][O:14][CH2:15][C:16]#[N:17]>>[CH3:12][N:10]([CH3:11])[CH:6]([N:7]([CH3:8])[CH3:9])[CH:15]([O:14][CH3:13])[C:16]#[N:17]

Participants

3

Reactant 2

HCID 74442MethoxyacetonitrileHCID 79885tert-Butoxy bis(dimethylamino)methane

Product 1

HCID 129674413,3-Bis(dimethylamino)-2-methoxypropanenitrileYield 33.2%

Procedure

360 g of 1-tert-butoxy-N,N,N′,N′-tetramethylmethanediamine (Bredereck's reagent) (2068 mmol, 1.0 eq.) and 150.0 g of methoxyacetonitrile (2068 mmol, 1.0 eq.) were stirred for 18 hours at 80° C. The reaction mixture was concentrated in vacuo. The residue was purified by vacuum distillation to yield 117 g (687 mmol, 33.0%) of the analytical pure target compound as a yellowish liquid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. distillationThe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-880f97d7b4a04ad493926842aab9eea1
Source dataset
uspto-grants-2016_08
Patent number
US09422268B2

Reaction notes

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