Triethylamine → HCID 178526609, compound

HRID 1747193Notes

Reaction equation

HRID 1747193 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-b992b1129da2436b859130e69afff44e
Source dataset
uspto-grants-2015_10
Patent number
US09150561B2

Reaction notes

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