Cyanogen Bromide → 5-[1-(4-Methoxyphenyl)cyclopropyl]-1,3,4-oxadiazol-2-amine

HRID 1099027Notes

Reaction equation

HRID 1099027 reaction equation
[N:1]#[C:2]Br.[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:15]([NH:17][NH2:18])=[O:16])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.C(=O)(O)[O-].[K+]>CO.O>[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2([C:15]3[O:16][C:2]([NH2:1])=[N:18][N:17]=3)[CH2:14][CH2:13]2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516893Potassium BicarbonateHCID 59216351HCID 59216351, compound

Product 1

HCID 592162905-[1-(4-Methoxyphenyl)cyclopropyl]-1,3,4-oxadiazol-2-amineYield 71.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Cyanogen bromide (0.424 g, 4.0 mmol) was added to an ice-cooled slurry of 1-(4-methoxyphenyl)cyclopropanecarbohydrazide (0.750 g, 3.64 mmol) and potassium bicarbonate (0.50 g, 5.0 mmol) in methanol (8 mL). The mixture was stirred at 0° C. for 1 h. the ice bath was allowed to warm slowly and stirred at RT for overnight. The reaction mixture was diluted with water (10 mL), stirred for 1 h. The precipitate was collected by filtration and washed with water, and dried on high vacuum to afford the desired product (600 mg, 71.3%). Analytical LCMS: (M+H)+=232.1.

Workup

  1. temperatureto warm slowly
  2. stirringstirred for 1 h
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried on high vacuum

Sources & evidence

ORD record
ord-b6609e07e7eb474ba61d5a396cf4cad1
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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