Dimethylformamide → 2-AMINOCARBONYL-5-NITROBENZOFURAN

HRID 1770833Notes

Reaction equation

HRID 1770833 reaction equation
[C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:7]=2[CH:8]=1)(O)=[O:2].C(Cl)Cl.C(Cl)(=O)C(Cl)=O.C[N:26](C=O)C>>[NH2:26][C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:7]=2[CH:8]=1)=[O:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 14771285-Nitrobenzofuran-2-carboxylic acid

Product 1

HCID 13829552-AMINOCARBONYL-5-NITROBENZOFURAN

Conditions

Temperature
10 °C

Procedure

A dry reaction flask equipped with a magnetic stirring bar, nitrogen inlet and rubber septum was charged with 2-carboxy-5-nitrobenzofuran (0.414 g, 2 mmol) and CH2Cl2 (100 mL). To this was added DMF (0.1 mL) followed by a slow addition of oxaloyl chloride (0.519 mL, 6 mmol) over the period of 5 minutes at 0° C. The reaction mixture was further stirred for 30 minutes by the time the formation of a clear solution was observed. The resulting clear solution was concentrated under a reduced pressure and dried under high vacuum for 30 minutes. The resulting residue was suspended in EtOAc (25 mL), cooled to 10° C., to it was added NH4OH (30% solution, 25 mL) and stirred at room temperature for 24 h. The organic phase was separated and dried over anhydrous sodium sulfate and solvent was removed to give 2-aminocarbonyl-5-nitrobenzofuran. 1H NMR (DMSO-d6): δ 8.75 (d, 1H, J=2.7 Hz), 8.28 (m, 2H), 7.86 (d, 1H, J=9.0 Hz), 7.83 (bs, 1H), 7.72 (s, 1H); LCMS: purity: 93%, MS (m/e): 206 (M+).

Workup

  1. customA dry reaction flask
  2. customequipped with a magnetic stirring bar, nitrogen inlet
  3. concentrationThe resulting clear solution was concentrated under a reduced pressure
  4. customdried under high vacuum for 30 minutes
  5. additionwas added NH4OH (30% solution, 25 mL)
  6. stirringstirred at room temperature for 24 h
  7. customThe organic phase was separated
  8. dry with materialdried over anhydrous sodium sulfate and solvent
  9. customwas removed

Sources & evidence

ORD record
ord-49cbb79b0d5b4d0b9c7a61a067df7d6e
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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