Acetic Anhydride → HCID 59540465, compound

HRID 923402Notes

Reaction equation

HRID 923402 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[C:22](=[O:24])[CH3:23])=[CH:20][CH:21]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 4558515HCID 4558515, compound

Product 1

HCID 59540465HCID 59540465, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of bis(4-nitrobenzyl)amine (500 mg, 1.741 mmol) in pyridine (9 mL) was slowly added acetic anhydride (0.18 mL, 1.92 mmol) via syringe. The resulting mixture was stirred at rt for 2 hours, and the reaction was concentrated in vacuo. The residue was dissolved in toluene and evaporated to dryness in vacuo. The residue was dissolved in 19:1 EtOAc:methanol, washed with water and brine, dried (Na2SO4), filtered and concentrated to afford the title compound (551 mg, 96%). MS (APCI) m/z 330.2 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionThe residue was dissolved in toluene
  3. customevaporated to dryness in vacuo
  4. dissolutionThe residue was dissolved in 19:1 EtOAc
  5. washmethanol, washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8671e1d4f7f84d1f986c64bf131b8c7a
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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