Sodium Bicarbonate → HCID 59212058, compound

HRID 655193Notes

Reaction equation

HRID 655193 reaction equation
[C:1]([CH2:4][N:5]([CH2:19][C:20]([OH:22])=[O:21])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)([OH:3])=O.C(=O)(O)[O-].[Na+]>C(OC(=O)C)(=O)C>[O:12]([C:8]1[CH:7]=[C:6]([N:5]2[CH2:19][C:20](=[O:21])[O:22][C:1](=[O:3])[CH2:4]2)[CH:11]=[CH:10][CH:9]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59212023HCID 59212023, compound

Product 1

HCID 59212058HCID 59212058, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

[Carboxymethyl-(3-phenoxyphenyl)amino]acetic acid 25 (5 g) was heated at reflux in acetic anhydride (30 mL) for 1 h. The cooled reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed several times with saturated aqueous sodium bicarbonate (until no further effervescence was observed) and twice with brine. The organic phase was dried (Na2SO4) and concentrated in vacuo to give the title compound as a golden oil (4.7 g, 100%). 1HNMR (300 MHz) (CDCl3) δ 6.10 (1H, m), 6.67 (2H, br d), 7.03 (2H, d), 7.17 (1H, t), 7.30 (1H, t) and 7.39 (2H, t).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed several times with saturated aqueous sodium bicarbonate (until no further effervescence
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26372794655543fb943d72588d01e1f5
Source dataset
uspto-grants-2011_12
Patent number
US08071582B2

Reaction notes

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