Hydrochloric Acid → 5-(Azetidin-3-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole hydrochloride

HRID 405788Notes

Reaction equation

HRID 405788 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)[O:10][N:9]=2)=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25].[ClH:27]>C(#N)C.O1CCOCC1>[ClH:27].[NH:15]1[CH2:14][CH:13]([C:11]2[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:24]([O-:26])=[O:25])[CH:4]=3)[N:12]=2)[CH2:16]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71281251HCID 71281251, compound

Product 1

HCID 712814215-(Azetidin-3-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole hydrochloride

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

To stirring suspension of tert-butyl 3-(3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (28) (1 g, 2.78 mmol) in acetonitrile (2 mL) was added 4 N HCl in dioxane (5 mL). The reaction was stirred at room temperature for 1 hour. The solvent was concentrated and the crude product was dried under high vacuum to yield 5-(azetidin-3-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole hydrochloride (29). MS m/z 261.4 (M+1)+.

Workup

  1. stirringThe reaction was stirred at room temperature for 1 hour
  2. concentrationThe solvent was concentrated
  3. dry with materialthe crude product was dried under high vacuum

Sources & evidence

ORD record
ord-6c8797c476014f38b7db9a4adcd07516
Source dataset
uspto-grants-2014_06
Patent number
US08754071B2

Reaction notes

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