Triethylamine → HCID 178526565, compound

HRID 1715245Notes

Reaction equation

HRID 1715245 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[N+:13]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([NH:22][NH2:23])=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[N+:13]([C:16]1[CH:25]=[CH:24][C:19]([C:20]2[O:21][C:1]([OH:2])=[N:23][N:22]=2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 3693744Benzoic acid, 4-nitro-, hydrazide

Product 1

HCID 178526565HCID 178526565, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (3.86 g; 23.81 mmol; 1 eq.) is added to a 0° C. solution of 4-nitrobenzohydrazide (4.31 g; 23.81 mmol; 1 eq.) and triethylamine (4.95 ml; 35.71 mmol; 1.50 eq.) in DMF (150 ml). The reaction mixture is stirred between 0° C. and rt for 3.5 hours. Solvents are removed under vacuo affording an orange oil which is solubilized in DCM and washed with HCl 0.1 M. The organic phase is concentrated. The resulting precipitate is recovered by filtration, affording 5-(4-nitrophenyl)-1,3,4-oxadiazol-2-ol as a white solid (4.50 g; 91%).

Workup

  1. customSolvents are removed under vacuo
  2. customaffording an orange oil which
  3. washwashed with HCl 0.1 M
  4. concentrationThe organic phase is concentrated
  5. filtrationThe resulting precipitate is recovered by filtration

Sources & evidence

ORD record
ord-1f29226b9cdd403690b14fce20cc6feb
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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