Dimethylformamide → 1-(1,2,4-Triazol-1-yl)-2,3-diphenyl-propan-2-ol

HRID 1982081Notes

Reaction equation

HRID 1982081 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[CH2:10](Cl)[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].[Cl-].[NH4+].N1C=[CH:25][N:24]=[N:23]1.[Na].[CH3:28][N:29](C)C=O>C(OCC)C>[N:24]1([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([OH:12])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:25]=[N:29][CH:28]=[N:23]1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 107572-ChloroacetophenoneHCID 25517Ammonium ChlorideHCID 5462224Magnesium2×HCID 178507080HCID 178507080, compound

Product 1

HCID 135184311-(1,2,4-Triazol-1-yl)-2,3-diphenyl-propan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Benzyl chloride (0.2 mol) was dissolved in dry diethyl ether (200 ml) and added dropwise to magnesium turnings (0.22 g atoms). After all the magnesium had reacted, the solution was refluxed for 1 hour and cooled to room temperature. Phenacyl chloride (0.1 mol) in dry diethyl ether (100 ml) was added dropwise over 1 hour at such a rate as to maintain gentle reflux. The solution was then refluxed for 2 hours, and cooled to room temperature; the mixture was poured into ice and the complex decomposed with ammonium chloride solution. The ethereal solution was washed several times with water (2×200 ml), dried (Na2SO4), and the solvent removed in vacuo to give, as a colourless oil, the crude chlorohydrin which was dissolved in dimethyl formamide (80 ml) and a solution of sodium triazole [prepared from sodium (0.1 g atoms) in methanol (40 ml) and 1,2,4-triazole (0.1 mole)] added dropwise at room temperature. After stirring at room temperature for 2 hours, the solution was warmed at 50° for 3 hours. The solvent was removed in vacuo and the residue poured into water to give a crystalline solid which was recrystallised from ethanol/petroleum ether to give the title compound, m.p. 124.5°.

Workup

  1. temperaturethe solution was refluxed for 1 hour
  2. temperatureto maintain gentle reflux
  3. temperatureThe solution was then refluxed for 2 hours
  4. temperaturecooled to room temperature
  5. additionthe mixture was poured into ice
  6. washThe ethereal solution was washed several times with water (2×200 ml)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent removed in vacuo
  9. customto give, as a colourless oil
  10. temperaturethe solution was warmed at 50° for 3 hours
  11. customThe solvent was removed in vacuo
  12. additionthe residue poured into water
  13. customto give a crystalline solid which
  14. customwas recrystallised from ethanol/petroleum ether

Sources & evidence

ORD record
ord-da3105bdb5f24baf83cfaea1d9650ac2
Source dataset
uspto-grants-1986_06
Patent number
US04595406

Reaction notes

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