Water → 1-(2-(3-azidopropyl)-5-(5-chloro-2-methylphenyl)-2-phenyl-1,3,4-oxadiazol-3(2H)-yl)-2,2-dimethylpropan-1-one

HRID 270524Notes

Reaction equation

HRID 270524 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7](=[N:14][NH:15][C:16](=[O:25])[C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[CH3:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[N+:2]=[N-:3].[C:26](Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].O>N1C=CC=CC=1>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:14]([C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[N:15]=[C:16]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[CH3:24])[O:25]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 86604839N'-(4-azido-1-phenylbutylidene)-5-chloro-2-methyl benzohydrazide

Product 1

HCID 866048401-(2-(3-azidopropyl)-5-(5-chloro-2-methylphenyl)-2-phenyl-1,3,4-oxadiazol-3(2H)-yl)-2,2-dimethylpropan-1-oneYield 50.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N′-(4-azido-1-phenylbutylidene)-5-chloro-2-methyl benzohydrazide (100 mg, 0.28 mmol) in pyridine (1 mL) was added pivaloyl chloride (70 μL, 0.56 mmol). After stirring at room temperature for 16 hours the heterogeneous mixture was treated with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic phases were washed successively with 10% NaHSO4 (2×10 mL), NaHCO3 (10 mL) and brine (10 mL) then dried over Na2SO4 and concentrated. The residue was purified by preparative TLC (9:1 hexanes/EtOAc) to afford the product (62 mg, 50%) as a colorless oil.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe combined organic phases were washed successively with 10% NaHSO4 (2×10 mL), NaHCO3 (10 mL) and brine (10 mL)
  3. dry with materialthen dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC (9:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-ed9da5885af74da5980ffd397073998d
Source dataset
uspto-grants-2008_11
Patent number
US07449486B2

Reaction notes

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