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1,3-Dibromopropane → 3-(3-Bromopropyl)-5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-oxadiazol-2(3H)-one

HRID 609891
Notes
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Reaction equation

HRID 609891 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[O:20][C:19](=[O:21])[NH:18][N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[Br:28][CH2:29][CH2:30][CH2:31]Br>CN(C)C=O>[Br:28][CH2:29][CH2:30][CH2:31][N:18]1[N:17]=[C:16]([C:7]2[CH:8]=[C:9]([C:12]([CH3:14])([CH3:15])[CH3:13])[C:10]([OH:11])=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=2)[O:20][C:19]1=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10340Sodium CarbonateHCID 1355035925-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-oxadiazol-2(3H)-one

Product 1

HCID 1357527423-(3-Bromopropyl)-5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-oxadiazol-2(3H)-oneYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-oxadiazol-2(3H)-one (0.50 g) in dimethylformamide (8 ml) were added sodium carbonate (0.36 g) and 1,3-dibromo-propane (1.74 g), followed by stirring at room temperature for 5 hours. After completion of the reaction, the reaction mixture was poured into ice-water, and the product was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform) and then recrystallized from chloroform/n-hexane to afford 0.45 g (63%) of the title compound as colorless crystals. mp 130-131° C. NMR (CDCl3) (200 MHz) δ: 1.46 (18H, s), 2.1-2.6 (2H, m), 3.46 (2H, t, J=6.6 Hz), 3.93 (2H, t,J=6.6 Hz), 5.60 (1H, s), 7.63 (2H, s)

Workup

  1. customAfter completion of the reaction
  2. extractionthe product was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; chloroform)
  6. customrecrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-c6ceab8309fc421aa2d20459064a55df
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05998452

Reaction notes

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