Benzyl Bromide → 2-(Benzylthio)-5-phenyl-1,3,4-oxadiazole

HRID 80417Notes

Reaction equation

HRID 80417 reaction equation
[C:1]1([C:7]2[O:11][C:10]([SH:12])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C>[CH2:22]([S:12][C:10]1[O:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][N:9]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 178527944HCID 178527944, compound

Product 1

HCID 28433352-(Benzylthio)-5-phenyl-1,3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 5-phenyl-[1,3,4]oxadiazole-2-thiol (3.1 g, 17.4 mmol; Aldrich) in ethanol (30 mL) was cooled to 0° C. and treated with diisopropylethylamine (3.1 mL, 17.4 mmol; Aldrich). The suspension cleared. Benzyl bromide (2.08 mL, 17.4 mmol; Aldrich) was then added, and the mixture was allowed to warm to room temperature. After 45 minutes, the resulting precipitate was collected by filtration and dried to afford the title compound.

Workup

  1. temperatureto warm to room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-612e26202f5b4b5f849e68095060fd5e
Source dataset
uspto-grants-2014_09
Patent number
US08846661B2

Reaction notes

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