2-Bromoethanol → HCID 57588283, compound

HRID 1782092Notes

Reaction equation

HRID 1782092 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)=[N:6][CH:7]=1.[OH-].[K+].Br[CH2:16][CH2:17][OH:18]>C(O)CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[N:10][N:11]([CH2:16][CH2:17][OH:18])[N:12]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 108982-Bromoethanol3×HCID 14797Potassium Hydroxide3×HCID 234386835-Bromo-2-(2H-tetrazol-5-yl)pyridine

Product 1

HCID 57588283HCID 57588283, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Conditions

Temperature
80 °C

Procedure

5-Bromo-2-(2H-tetrazol-5-yl)pyridine (WO 0194342 A1) (1.2 g, 5.3 mmol) was dissolved/suspended in 1-propanol (15 ml), a solution of potassium hydroxide (250 mg, 4.5 mmol) in 1-propanol (15 ml) was added and it was heated at 80° C. for 1 hour. 2-Bromoethanol (0.344 ml, 4.8 mmol) was added and it was refluxed for one day. Further potassium hydroxide (270 mg) and 2-bromoethanol (0.35 ml) were added and the mixture was heated for another 4 hours at reflux. Further potassium hydroxide and 2-bromoethanol were added once more and the mixture was refluxed for 14 hours. The reaction mixture was filtered through a 0.45 μM membrane and the filter cake was washed with ethanol and dichloromethane. Chromatography on silica gel with hexanes/ethyl acetate 1:1 to ethyl actetate gave 0.342 g of the title compound (24%), together with 0.225 g of the corresponding 1H-tetrazole regioisomer.

Workup

  1. temperatureit was refluxed for one day
  2. temperaturethe mixture was heated for another 4 hours
  3. temperatureat reflux
  4. temperaturethe mixture was refluxed for 14 hours
  5. filtrationThe reaction mixture was filtered through a 0.45 μM membrane
  6. washthe filter cake was washed with ethanol and dichloromethane

Sources & evidence

ORD record
ord-be20d78bd782404d815629aba0e2d753
Source dataset
uspto-grants-2009_03
Patent number
US07498350B2

Reaction notes

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