2-Bromoethanol → HCID 86745601, compound

HRID 2372810Notes

Reaction equation

HRID 2372810 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[NH:19][N:18]=[N:17][N:16]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Br[CH2:23][CH2:24][OH:25]>C(O)CC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:19]([CH2:23][CH2:24][OH:25])[N:18]=[N:17][N:16]=3)=[CH:11][CH:10]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 108982-BromoethanolHCID 178491281HCID 178491281, compound

Product 1

HCID 86745601HCID 86745601, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To 30 ml of n-propanol are added 10-2 mole of 5-[4-(4-methoxy benzyloxy) phenyl] tetrazole and 10-2 mole of 2-bromo ethanol. The mixture is heated to reflux for 25 hours. The solvent is evaporated and the residue taken up in 100 ml of hot ether. The etherated solution is washed with 0.5N NaOH, then with water. After drying on sodium sulfate, the etherated phase is concentrated. The compound of code number 42 is obtained after recrystallization in methanol. The recrystallization solvent is concentrated and the residue is subjected to chromatography on a silica column (eluent:ethyl acetate/petroleum ether:1/4) whereby the compound of code number 51 is isolated.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 25 hours
  3. customThe solvent is evaporated
  4. washThe etherated solution is washed with 0.5N NaOH
  5. customAfter drying on sodium sulfate
  6. concentrationthe etherated phase is concentrated
  7. customThe compound of code number 42 is obtained
  8. customafter recrystallization in methanol
  9. concentrationThe recrystallization solvent is concentrated
  10. customis isolated

Sources & evidence

ORD record
ord-79d4709302a9403aa3efacef8a2763ec
Source dataset
uspto-grants-1992_03
Patent number
US05100910

Reaction notes

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