Triethylamine → HCID 90411153, compound

HRID 2170838Notes

Reaction equation

HRID 2170838 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][C:10]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[O:11])=[C:4]([CH3:17])[CH:3]=1.C(N(CC)CC)C.[C:25](N1C=CN=C1)(N1C=CN=C1)=[O:26]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:9]=[C:10]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)[O:11][C:25]2=[O:26])=[C:4]([CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 90412415HCID 90412415, compound

Product 1

HCID 90411153HCID 90411153, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N′-(4-chloro-2-methylphenyl)furan-2-carbohydrazide (0.5 mmol), triethylamine (0.1 mL, 0.75 mmol), and carbonyldiimidazole (0.24 g, 1.5 mmol) was stirred at 80° C. in 2 mL of THF overnight. The crude product obtained after removal of the solvent was then subject to chromatography (silica gel, 1:9 ethyl acetate-hexanes), followed by crystallization from hexanes to provide 83 mg (0.3 mmol, yield 60%) of 3-(4-Chloro-2-methyl-phenyl)-5-furan-2-yl-3H-[1,3,4]oxadiazol-2-one as a white solid with an HPLC purity of 98.9%. LC-MS [M+H] 277.9 (C13H9ClN2O3+H, expected 277.68). The 1H-NMR spectrum was in accordance with the chemical structure.

Workup

  1. customThe crude product obtained
  2. customafter removal of the solvent
  3. customfollowed by crystallization from hexanes

Sources & evidence

ORD record
ord-1c9cc18585084b8da1279255d8e1931d
Source dataset
uspto-grants-2015_06
Patent number
US09051309B2

Reaction notes

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