Lithium iodide → 4-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoic acid

HRID 2172167Notes

Reaction equation

HRID 2172167 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13](=[O:15])[N:12]([CH2:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[I-].[Li+]>N1C=CC=CC=1.O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:14][C:13](=[O:15])[N:12]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=3)[N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 66321Lithium iodideHCID 66616181methyl 4-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoate

Product 1

HCID 581569334-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoic acidYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Methyl 4-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoate (50 mg, 0.14 mmol) is refluxed with lithium iodide (0.19 g, 1.4 mmol) in pyridine (5 mL) for 48 h and the mixture is diluted with water (30 mL) after cooling to room temperature. The precipitate is collected by filtration, washed with dichloromethane and dried in the air to furnish the desired product 4-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoic acid (31 mg, 66%), m.p. 217-219° C. 1H NMR (CDCl3, 300 MHz) δ (ppm) 1.13 (d, 6H) 2.70-2.90 (m, 1H), 4.86 (s, 2H), 7.17 (d, 2H), 7.30 (d, 2H), 7.59 (d, 2H), 7.89 (d, 2H). MS (ES+): m/e 339.

Workup

  1. filtrationThe precipitate is collected by filtration
  2. washwashed with dichloromethane
  3. customdried in the air

Sources & evidence

ORD record
ord-c6dcfd65ce244f888850b25e19be5a9d
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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