Potassium Carbonate → Ethyl 3-amino-6-nitro-1-benzothiophene-2-carboxylate

HRID 1425265Notes

Reaction equation

HRID 1425265 reaction equation
[N+]([C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.C(=O)([O-])[O-].[K+].[K+].[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH2:22][SH:23]>CN(C=O)C>[NH2:7][C:6]1[C:5]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:4]=2[S:23][C:22]=1[C:21]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 5540822,4-Dinitrobenzonitrile

Product 1

HCID 67549245Ethyl 3-amino-6-nitro-1-benzothiophene-2-carboxylateYield 32.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4-Dinitrobenzonitrile (5.08 g, 26.3 mmol) was dissolved in DMF (55 ml). Potassium carbonate (4.36 g, 31.6 mmol) and ethyl thioglycolate (3.17 g, 26.3 mmol) were added, and the mixture was stirred at room temperature for three days. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was recrystallized from ethyl acetate/hexane to obtain 2.27 g of the title compound as crystals (32%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentration under reduced pressure
  6. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1dd42d358bb04845b5ea886624ce172c
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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