Dimethylformamide dimethyl acetal → HCID 10975874, compound

HRID 1478238Notes

Reaction equation

HRID 1478238 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][N+:6]#[C-:7])[CH3:2].CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>C(O)C>[CH2:1]([O:3][C:4](=[O:8])/[C:5](/[N+:6]#[C-:7])=[CH:11]/[N:12]([CH3:14])[CH3:13])[CH3:2]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 533707Ethyl isocyanoacetate

Product 1

HCID 10975874HCID 10975874, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl-2-isocyanoacetate (10.3 g, 91 mmol) in ethanol (100 ml) was cooled down to 0° C. 1,1-dimethoxy-N,N-dimethyl methanamine (26.6 ml, 200 mmol) was added and the reaction mixture was then allowed to reach RT and stirred for 24 h. The mixture was concentrated and the crude material was purified by flash chromatography (heptane/EtOAc, 100:0 to 40:60) to afford 11 g (64.7 mmol, 71.1% yield) of the title compound. LCMS: (M+H)=169; tR=0.74 min (LC-MS 2); 1H-NMR (CDCl3, 400 MHz) δ (ppm) 7.15 (s, 1H), 4.18 (q, 2H), 3.20 (bs, 6H), 1.26 (t, 3H).

Workup

  1. customto reach RT
  2. concentrationThe mixture was concentrated
  3. customthe crude material was purified by flash chromatography (heptane/EtOAc, 100:0 to 40:60)

Sources & evidence

ORD record
ord-07c576ca91d9475181cce6374cdb3277
Source dataset
uspto-grants-2016_08
Patent number
US09403827B2

Reaction notes

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