Benzoyl chloride → 2-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylmethyl]-5-phenyl-[1,3,4]oxadiazole

HRID 1183280Notes

Reaction equation

HRID 1183280 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][C:15]([NH:17][NH2:18])=[O:16])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26](Cl)(=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1(C)C(S(Cl)(=O)=O)=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][C:15]2[O:16][C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:18][N:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 66577599[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-acetic acid hydrazide

Product 1

HCID 665793162-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylmethyl]-5-phenyl-[1,3,4]oxadiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-acetic acid hydrazide (0.142 g, 0.46 mmol) in CH2Cl2 (2.3 mL) at 0° C. was added triethylamine (0.19 mL, 1.37 mmol) and benzoyl chloride (0.05 mL, 0.46 mmol), and the reaction was stirred at room temperature for 3 hours. Toluenesulfonyl chloride (0.088 g, 0.46 mmol) was added, and the reaction was stirred overnight. After aqueous workup, the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. stirringthe reaction was stirred overnight
  2. customAfter aqueous workup, the crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3fc7ab5e8ea042aa8ea01cd9b29be352
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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