Sodium Hydroxide → methyl 4-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoate

HRID 2172166Notes

Reaction equation

HRID 2172166 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13](=[O:15])[NH:12][N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-:16].[Na+]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13](=[O:15])[N:12]([CH2:1][C:4]3[CH:9]=[CH:8][C:7]([C:10]([O:14][CH3:13])=[O:16])=[CH:6][CH:5]=3)[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 3129205-(4-isopropylphenyl)-1,3,4-oxadiazol-2(3H)-one

Product 1

HCID 66616181methyl 4-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoateYield 184.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

5-(4-Isopropylphenyl)-1,3,4-oxadiazol-2(3H)-one (0.41 g, 2.0 mmol) is dissolved in dichloromethane (5 mL) and stirred vigorously with methyl 4-bromomethylbenoate (0.50 g, 2.2 mmol) in the presence of sodium hydroxide (1.25 N, 1.76 mL, 2.2 mmol) and tetra-n-butylammonium bromide (0.07 g, 0.022 mmol) at room temperature overnight. The solvent is removed in vacuum, and the residue is treated with water. The precipitate is collected by filtration, washed with hexanes thoroughly and dried in the air to provide methyl 4-{[5-(4-isopropylphenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]methyl}benzoate (0.65 g, 93%). (ES+): m/e 353.

Workup

  1. customThe solvent is removed in vacuum
  2. additionthe residue is treated with water
  3. filtrationThe precipitate is collected by filtration
  4. washwashed with hexanes thoroughly
  5. customdried in the air

Sources & evidence

ORD record
ord-14d01feb264c4a4da670e1f9b4bfb180
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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