Ammonium Hydroxide → 2-[1-(3-Bromo-phenyl)-1H-imidazol-4-yl]-5-methyl-[1,3,4]oxadiazole

HRID 2266409Notes

Reaction equation

HRID 2266409 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[N:9]=[CH:10][N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=2)[CH:12]=1)=[O:7])(=O)[CH3:2].[NH4+].[OH-]>>[Br:19][C:15]1[CH:14]=[C:13]([N:11]2[CH:12]=[C:8]([C:6]3[O:7][C:1]([CH3:2])=[N:4][N:5]=3)[N:9]=[CH:10]2)[CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 577508851-(3-Bromo-phenyl)-1H-imidazole-4-carboxylic acid N'-acetyl-hydrazide

Product 1

HCID 161285892-[1-(3-Bromo-phenyl)-1H-imidazol-4-yl]-5-methyl-[1,3,4]oxadiazole

Conditions

Temperature
155 °C

Procedure

A suspension of 6 (50 mg, 0.15 mmol) in PPA was heated to 155° C. for 1 h and then allowed to cool to room temperature. the reaction mixture was carefully diluted using 6% NH4OH aqueous solution to pH=8. The precipitate formed was isolated by filtration to afford 715 mg (33%) as a white solid. HRMS (ESI+): m/z=305.1341 [M+H]

Workup

  1. temperatureto cool to room temperature
  2. additionthe reaction mixture was carefully diluted
  3. customThe precipitate formed
  4. customwas isolated by filtration
  5. customto afford 715 mg (33%) as a white solid

Sources & evidence

ORD record
ord-6b2dba40913c4e6b832dd96e404048d6
Source dataset
uspto-grants-2010_12
Patent number
US07858649B2

Reaction notes

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