Cyanogen Bromide → 4-[(5-Amino-1,3,4-oxadiazol-2-yl)methyl]phenol

HRID 1822889Notes

Reaction equation

HRID 1822889 reaction equation
Br[C:2]#[N:3].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([NH:14][NH2:15])=[O:13])=[CH:7][CH:6]=1>CO.O>[NH2:3][C:2]1[O:13][C:12]([CH2:11][C:8]2[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=2)=[N:14][N:15]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 37318662-(4-Hydroxyphenyl)acetohydrazide

Product 1

HCID 219193154-[(5-Amino-1,3,4-oxadiazol-2-yl)methyl]phenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

Solid BrCN 6.059 g (57.2 mmol) was added in one portion into ice-cooled slurry of (4-hydroxy-phenyl)-acetic acid hydrazide 8.642 g (52.0 mmol) and KHCO3 6.510 g (65 mmol) in MeOH (100 mL). The mixture was stirred at 0-5° C. for 1 hour, the ice bath allowed to melt and stirred at room temperature overnight (18 hr). The reaction mixture was diluted with water (100 mL), stirred for 1 hour, the precipitate was collected by filtration, washed with water and dried on high vacuum. A second fraction precipitated after concentrating and cooling the supernatants.

Workup

  1. stirringstirred at room temperature overnight (18 hr)
  2. stirringstirred for 1 hour
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water
  5. customdried on high vacuum
  6. customA second fraction precipitated
  7. concentrationafter concentrating
  8. temperaturecooling the supernatants

Sources & evidence

ORD record
ord-7b2aa49c5bc340b087a376f9edc1fc9b
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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