Aniline → HCID 23130662, compound

HRID 2080110Notes

Reaction equation

HRID 2080110 reaction equation
[C:1]1([NH:7][CH2:8][C:9]2[O:13][C:12]([CH2:14][O:15]C(=O)C)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]1([NH:7][CH2:8][C:9]2[O:13][C:12]([CH2:14][OH:15])=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 67119680HCID 67119680, compound

Product 1

HCID 23130662HCID 23130662, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, the resulting mixture of acetic acid 5-phenylaminomethyl-furan-2-ylmethyl ester and aniline (2.91 g) as well as potassium carbonate (3.28 g, 23.7 mmol) were suspended in methanol (60 mL), and the solution was stirred overnight at room temperature. The reaction solution was evaporated in vacuo, water and ethyl acetate were added to the residue, the organic layer was partitioned, washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (1.99 g, 9.79 mmol, 82%) was obtained as a colorless oil.

Workup

  1. customThe reaction solution was evaporated in vacuo, water and ethyl acetate
  2. additionwere added to the residue
  3. customthe organic layer was partitioned
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ee9df74de2bb4c8692271236a144b11c
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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