tert-Butoxy bis(dimethylamino)methane → HCID 57453860, compound

HRID 906397Notes

Reaction equation

HRID 906397 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.C(O[CH:16](N(C)C)[N:17]([CH3:19])[CH3:18])(C)(C)C>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4](/[CH:10]=[CH:16]/[N:17]([CH3:19])[CH3:18])[CH:3]=1

Participants

3

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 1442674-Bromo-2-methylbenzonitrile

Product 1

HCID 57453860HCID 57453860, compound

Conditions

Temperature
140 °C

Procedure

A solution of 4-bromo-2-methylbenzonitrile (1.0 g) dissolved in 1-tert-butoxy-N,N,N′,N′-tetramethylmethanediamine (2.11 ml) was stirred at 140° C. for 2 h (flask open to evaporate t-butanol). The reaction mixture was diluted with water (250 mL), and extracted with ethyl acetate (350 mL). The organic was dried (MgSO4), filtered and evaporated to afford the crude product. The crude product was triturated with isohexane overnight to afford the subtitle compound (0.75 g) as a solid.

Workup

  1. custom(flask open to evaporate t-butanol)
  2. additionThe reaction mixture was diluted with water (250 mL)
  3. extractionextracted with ethyl acetate (350 mL)
  4. dry with materialThe organic was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto afford the crude product
  8. customThe crude product was triturated with isohexane overnight

Sources & evidence

ORD record
ord-dfbb4059340f4f4584861fdf7c815a21
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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