Hydrazine → 3-(3-Benzyl-1,2,4-oxadiazol-5-yl)propanohydrazide

HRID 249786Notes

Reaction equation

HRID 249786 reaction equation
[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][CH2:14][C:15]([OH:17])=O)[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:30][NH2:31]>C1COCC1>[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][CH2:14][C:15]([NH:30][NH2:31])=[O:17])[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 682631,1'-CarbonyldiimidazoleHCID 398703933-(3-Benzyl-1,2,4-oxadiazol-5-yl)propanoic acid

Product 1

HCID 598538253-(3-Benzyl-1,2,4-oxadiazol-5-yl)propanohydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-benzyl-1,2,4-oxadiazol-5-yl)propanoic acid (1.0 g, 4.3 mmol) in THF (15 mL) was added N,N-carbonyldiimidazole (0.77 g, 4.7 mmol). After refluxing for 2 hours, hydrazine (0.6 g, 20 mmol) was added to the reaction mixture slowly with syringe at 0° C. The reaction mixture was allowed to warm to room temperature slowly and then concentrated to yield the desired product as white solid. LCMS calculated for C12H15N4O2 (M+H): 247.1. found: 247.1.

Workup

  1. temperatureAfter refluxing for 2 hours
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-50d39b2d6a5145f293176d4884cc1acd
Source dataset
uspto-grants-2011_01
Patent number
US07863285B2

Reaction notes

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