Triethylamine → HCID 178526609, compound

HRID 1715242Notes

Reaction equation

HRID 1715242 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[N+:13]([C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19]([NH:21][NH2:22])=[O:20])([O-:15])=[O:14].C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[N+:13]([C:16]1[CH:17]=[C:18]([C:19]2[O:20][C:1]([OH:2])=[N:22][N:21]=2)[CH:23]=[CH:24][CH:25]=1)([O-:15])=[O:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 32914983-Nitrobenzohydrazide

Product 1

HCID 178526609HCID 178526609, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (641.2 mg; 3.95 mmol; 1 eq.) is added to a 0° C. solution of 3-nitrobenzohydrazide (715.9 mg; 3.95 mmol; 1 eq.) and triethylamine (822 μl; 5.93 mmol; 1.50 eq.) in DMF (30 ml). The reaction mixture is stirred between 0° C. and rt for 4 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-(3-nitrophenyl)-1,3,4-oxadiazol-2-ol as a white solid (469.9 mg; 58%). 1H NMR (DMSO-d6) δ: 7.84 (s, 1H), 8.19 (m, 1H), 8.41 (m, 2H), 12.91 (s, 1H). HPLC (method A), Rt: 2.06 min (purity: 97.5%).

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-7e0928c133d84adbb0ff80347631647a
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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