Benzyl Bromide → 2-Benzylsulfanyl-5-(5-bromo-furan-2-yl)-[1,3,4]oxadiazole

HRID 386401Notes

Reaction equation

HRID 386401 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[O:14][C:13]([C:15]2[O:19][C:18]([SH:20])=[N:17][N:16]=2)=[CH:12][CH:11]=1.C(N(CC)CC)C.[OH-].[Na+]>O.C(O)C>[CH2:1]([S:20][C:18]1[O:19][C:15]([C:13]2[O:14][C:10]([Br:9])=[CH:11][CH:12]=2)=[N:16][N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 1785279415-(5-Bromo-furan-2-yl)-[1,3,4]oxadiazole-2-thiol

Product 1

HCID 672800602-Benzylsulfanyl-5-(5-bromo-furan-2-yl)-[1,3,4]oxadiazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Benzylbromide (6.18 g, 36.1 mmol) was added over 5 minutes time-period to a mixture of 5-(5-bromo-furan-2-yl)-[1,3,4]oxadiazole-2-thiol (8.5 g, 36.1 mmol), trietylamine (6.96 g, 68.8 mmol) and ethanol (100 ml, 99%). The reaction mixture was stirred at room-temperature for 2 hours. Aqueous sodium hydroxide (50 ml, 1 M) and water (100 ml) was added followed by extraction with diethylether (3×50 ml). The organic phase was washed with water (3×50 ml), dried and evaporated. The product was isolated as a red solid. Yield 10.7 g (92%).

Workup

  1. extractionfollowed by extraction with diethylether (3×50 ml)
  2. washThe organic phase was washed with water (3×50 ml)
  3. customdried
  4. customevaporated
  5. customThe product was isolated as a red solid

Sources & evidence

ORD record
ord-05d802136e924f6d848d8fe10a3943b0
Source dataset
uspto-grants-2013_02
Patent number
US08372832B2

Reaction notes

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