Diethyl Ether → HCID 21976145, compound

HRID 11733Notes

Reaction equation

HRID 11733 reaction equation
C([O:3][C:4](=[O:23])[C:5]([N:7]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[CH3:22])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6])C.[OH-].[Na+].C(OCC)C>C1COCC1>[C:15]1([CH3:22])[CH:16]=[C:17]([CH3:21])[CH:18]=[C:19]([CH3:20])[C:14]=1[N:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5](=[O:6])[C:4]([OH:23])=[O:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 68526436HCID 68526436, compound

Product 1

HCID 21976145HCID 21976145, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(Mesityl)-oxanilic acid ethyl ester (1.99 g, 8.5 mmol) was dissolved in THF (50 ml), forming a solution. To this solution was added 1M NaOH solution (40 ml), and the mixture was then stirred for 2 hours. Diethyl ether (25 ml) was then added, and the layers were separated. The organic layer was washed with 1M NaOH solution (40 ml). The aqueous layer was then acidified with 2M HCl until precipitation occurred. The precipitate was then extracted with ethyl acetate (2×50 ml). The ethyl acetate was washed with brine (50 ml), and then dried over MgSO4. Removal of the solvent under reduced pressure provided the product as a white solid (1.74 g, 8.4 mmol, 99% yield). 1H NMR (300 MHz, CDCl3) δ 8.51 (s, 1H), 6.93 (s, 2H), 2.29 (s,3H), 2.19 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 160.0, 156.1, 138.6, 134.7, 129.5, 128.9, 21.2, 18.5. Anal. Calcd for C11H13NO3: C, 63.76; H, 6.32; N, 6.76. Found: C, 63.59; H, 6.32; N, 6.79.

Workup

  1. customforming a solution
  2. customthe layers were separated
  3. washThe organic layer was washed with 1M NaOH solution (40 ml)
  4. customThe aqueous layer was then acidified with 2M HCl until precipitation
  5. extractionThe precipitate was then extracted with ethyl acetate (2×50 ml)
  6. washThe ethyl acetate was washed with brine (50 ml)
  7. dry with materialdried over MgSO4
  8. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-c6e621c644b942a3ac0c477411b26a0c
Source dataset
uspto-grants-2006_08
Patent number
US07098278B2

Reaction notes

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