Triethylamine → HCID 178526609, compound

HRID 2405122Notes

Reaction equation

HRID 2405122 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 (641.18 mg; 3.95 mmol; 1.00 eq.) is added to a 0° C. solution of 3-nitrobenzohydrazide (715.90 mg; 3.95 mmol; 1.00 eq.) and triethylamine (822.18 μl; 5.93 mmol; 1.50 eq.) in DMF (30.00 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 (469.90 mg; 58%).

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-688a7e9cae3e4cfaa78fde9613a704c8
Source dataset
uspto-grants-2014_08
Patent number
US08802861B2

Reaction notes

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