Ethanol → HCID 21891612, compound

HRID 720344

Reaction equation

HRID 720344 reaction equation
[N+:1]([C:4]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[C:10]([O:17][CH3:18])=[CH:9][C:5]=1C(O)=O)([O-:3])=[O:2].C([N:21]([CH2:24]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[CH2:43]([OH:45])[CH3:44]>C1C=CC=CC=1>[CH2:43]([O:45][C:24]([NH:21][C:5]1[CH:9]=[C:10]([O:17][CH3:18])[C:11]([O:15][CH3:16])=[C:12]([O:13][CH3:14])[C:4]=1[N+:1]([O-:3])=[O:2])=[O:33])[CH3:44]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 971163,4,5-Trimethoxy-2-nitrobenzoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 21891612HCID 21891612, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Nitro-3,4,5-trimethoxybenzoic acid (4.7 g) was dissolved in dry benzene (70 mL), triethylamine (2.56 mL) and diphenylphosphoryl azide (4.15 mL) were added to the solution, and the mixture was stirred for 2 hours under reflux. Dry ethanol (140 mL) was added to the reaction mixture, and the mixture was further stirred overnight under reflux. After the reaction mixture was concentrated under reduced pressure, the residue was extracted with ethyl acetate. The resultant organic layer was washed with diluted hydrochloric acid, an aqueous solution of potassium carbonate, water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4 to 1:3) to obtain the title compound.

Workup

  1. temperatureunder reflux
  2. waitthe mixture was further stirred overnight
  3. temperatureunder reflux
  4. concentrationAfter the reaction mixture was concentrated under reduced pressure
  5. extractionthe residue was extracted with ethyl acetate
  6. washThe resultant organic layer was washed with diluted hydrochloric acid
  7. dry with materialan aqueous solution of potassium carbonate, water and saturated brine, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4 to 1:3)

Sources & evidence

ORD record
ord-612597d7f3004cada9b8e7790d6814f1
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Linked notes

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