tert-Butoxy bis(dimethylamino)methane → HCID 68839019, compound

HRID 491495Notes

Reaction equation

HRID 491495 reaction equation
[I:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([I:14])=[CH:8][C:3]=1[O:4][CH2:5][C:6]#[N:7].[C:15](OC(N(C)C)N(C)C)(C)(C)[CH3:16]>>[I:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([I:14])=[CH:8][C:3]=1[O:4][C:5](=[CH:15][CH3:16])[C:6]#[N:7]

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 57678433HCID 57678433, compound

Product 1

HCID 68839019HCID 68839019, compoundYield 116.6%

Conditions

Temperature
105 °C

Procedure

(2,5-Diiodo-4-methoxy-phenoxy)-acetonitrile (2.8 g, 6.75 mmol) and tert-butoxybis(dimethylamino)methane (Bredrick's reagent, 7 mL, 33.7 mmol) were combined and heated to 105° C. under nitrogen for 2 hours. The reaction mixture was cooled and concentrated under reduced pressure to yield 3.47 g of crude 2-(2,5-diiodo-4-methoxy-phenoxy)-but-2-enenitrile, which was used directly in the following step.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f97a0dec9e874573b15cf9c2943c2337
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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