Lithium iodide → 3-[3-(4-TERT-BUTYLPHENYL)-UREIDO]-BENZOIC ACID

HRID 600918Notes

Reaction equation

HRID 600918 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)=[O:12])[CH:5]=1.[I-].[Li+]>N1C=CC=CC=1>[C:20]([C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:11](=[O:12])[NH:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:24])=[O:2])=[CH:19][CH:18]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 66603157HCID 66603157, compound

Product 1

HCID 28121013-[3-(4-TERT-BUTYLPHENYL)-UREIDO]-BENZOIC ACIDYield 67.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl-3-[3-(4-tert-butylphenyl)-ureido]-benzoate (0.19 g, 0.58 mmol) in pyridine (15 mL) was treated with anhydrous lithium iodide (0.78 g, 6.0 mmol), and the resulting solution was heated to reflux for 20 h. The solution was cooled and partially evaporated, and the residual material was partitioned between 1 N aq. HCl and ethyl acetate. The aqueous layer was extracted with more ethyl acetate, and the organic extracts were washed with brine, combined, dried over magnesium sulfate, filtered, and evaporated. The remaining powdery solid was triturated with ether, collected by filtration and dried under vacuum to afford the title compound (0.12 g, 0.39 mmol, 66%). m.p. 147-148° C. 1H NMR (d6-DMSO, 300 MHz): d 8.58 (1H, s), 8.10 (1H, t, J=2 Hz), 7.72-7.62 (2H, m), 7.40-7.25 (5H,m), 6.53 (1H, s), 1.25 (9H, s).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 20 h
  3. temperatureThe solution was cooled
  4. custompartially evaporated
  5. customthe residual material was partitioned between 1 N aq. HCl and ethyl acetate
  6. extractionThe aqueous layer was extracted with more ethyl acetate
  7. washthe organic extracts were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe remaining powdery solid was triturated with ether
  12. filtrationcollected by filtration
  13. customdried under vacuum

Sources & evidence

ORD record
ord-b4ecbeff0b7642f4b805668a3ef7d84c
Source dataset
uspto-grants-2011_03
Patent number
US07902241B2

Reaction notes

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