Lithium iodide → Benzoic acid, 3-[3-[4-(1-methylethyl)phenyl]-2,4-dioxo-1-imidazolidinyl]-

HRID 2194822Notes

Reaction equation

HRID 2194822 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH2:13][N:12]([C:16]3[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=3)[C:19]([O:21]C)=[O:20])[C:11]2=[O:26])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[I-].[Li+]>N1C=CC=CC=1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[CH2:13][N:12]([C:16]3[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=3)[C:19]([OH:21])=[O:20])[C:11]2=[O:26])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 66603368HCID 66603368, compound

Product 1

HCID 10449779Benzoic acid, 3-[3-[4-(1-methylethyl)phenyl]-2,4-dioxo-1-imidazolidinyl]-Yield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl 3-[1-(4-isopropylphenyl)-2,5-dioxo-imidazolidin-3-yl]-benzoate (0.30 g, 0.85 mmol) in pyridine (2 mL) was treated with anhydrous lithium iodide (1.5 g, 11.2 mmol), and the resulting mixture was heated to reflux for 4 h. The solution was cooled, evaporated and partitioned between ethyl acetate and 1N aq. HCl. The aqueous layer was extracted with more ethyl acetate, and the extracts were washed with satd. aq. brine, combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the title product as a solid (0.21 g, 0.62 mmol, 73%), m.p. 249-252° C. 1H NMR (d6-DMSO, 300 MHz): d 13.09 (1H, br), 8.29 (1H, t, J=2 Hz), 7.82 (1H, d, J=8 Hz), 7.72 (1H, d, J=8 Hz), 7.56 (1H, t, J=8 Hz), 7.38 (2H, d, J=8 Hz), 7.31 (2H, d, J=8 Hz), 4.62 (2H, s), 2.96 (1H, m, J=7 Hz), 1.22 (6H, d, J=7 Hz). Mass spectrum (ES+): m/z 340 (18), 339 (100). Elemental analysis: calculated for C19H18N2O4 C, 67.45; H, 5.32; N, 8.28; observed C, 67.26; H, 5.10; N, 8.12.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 4 h
  3. temperatureThe solution was cooled
  4. customevaporated
  5. custompartitioned between ethyl acetate and 1N aq. HCl
  6. extractionThe aqueous layer was extracted with more ethyl acetate
  7. washthe extracts were washed with satd
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-3d6671c02204474882d32803b5cacf51
Source dataset
uspto-grants-2012_12
Patent number
US08334313B2

Reaction notes

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