3-Oxobutyronitrile → 5-(Dimethylamino)-2-(dimethylaminomethylidene)-3-oxopent-4-enenitrile

HRID 506170Notes

Reaction equation

HRID 506170 reaction equation
[C:1](#[N:6])[CH2:2][C:3]([CH3:5])=[O:4].C(O[CH:12]([N:16]([CH3:18])[CH3:17])N(C)C)(C)(C)C.[CH3:19][N:20]([CH:22](OC)OC)[CH3:21]>>[CH3:18][N:16]([CH3:17])[CH:12]=[CH:5][C:3](=[O:4])[C:2](=[CH:19][N:20]([CH3:22])[CH3:21])[C:1]#[N:6]

Participants

4

Reactant 3

HCID 755793-OxobutyronitrileHCID 78373Dimethylformamide dimethyl acetalHCID 79885tert-Butoxy bis(dimethylamino)methane

Product 1

HCID 722970555-(Dimethylamino)-2-(dimethylaminomethylidene)-3-oxopent-4-enenitrileYield 67.5%

Conditions

Temperature
100 °C

Procedure

A mixture of acetoacetonitrile (41 g, 493 mmol), t-butoxybis(dimethyl amino)methane (86 g, 493 mmol) and DMF-DMA (263 mL, 1.97 mol) was heated at 100° C. overnight and evaporated to remove the volatiles. The residue was triturated with hexanes/ether (1:1) and the solids were collected by filtration and washed with hexanes/ether (1:1) and a minimum amount of EtOAc to give 64.3 g (67%) of 5-(dimethylamino)-2-[(dimethylamino)methylene]-3-oxopent-4-enenitrile as a light yellow solid, which was used for the next step without further purification.

Workup

  1. customevaporated
  2. customto remove the volatiles
  3. customThe residue was triturated with hexanes/ether (1:1)
  4. filtrationthe solids were collected by filtration
  5. washwashed with hexanes/ether (1:1)

Sources & evidence

ORD record
ord-c6005b4fad4544b394938890aa4465f5
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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