Dimethylformamide dimethyl acetal → methyl (E)-5-(2-dimethylaminovinyl)-4-nitrothiophene-2-carboxylate

HRID 1442539Notes

Reaction equation

HRID 1442539 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[S:7][C:8]=1[CH3:9])([O-:3])=[O:2].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[CH3:16][N:17]([CH3:19])/[CH:18]=[CH:9]/[C:8]1[S:7][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 268679Methyl 5-methyl-4-nitrothiophene-2-carboxylate

Product 1

HCID 12110978methyl (E)-5-(2-dimethylaminovinyl)-4-nitrothiophene-2-carboxylateYield 96%

Procedure

A solution of methyl 4-nitro-5-methylthiophene-2-carboxylate (23 g, 114 mmol) in N,N-dimethylformamide dimethyl acetal (115 ml) was stirred at 110° C. for 1 hr. The reaction mixture was cooled to room temperature, concentrated under reduced pressure to about half amount, and poured into water (500 ml). The precipitated solid was collected by filtration, washed with water (500 ml×2), and dried under reduced pressure to give methyl (E)-5-(2-dimethylaminovinyl)-4-nitrothiophene-2-carboxylate (28 g, yield 96%).

Workup

  1. concentrationconcentrated under reduced pressure to about half amount
  2. additionpoured into water (500 ml)
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water (500 ml×2)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a63ca5c3f36f4211ac99eb918c876544
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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