Water → HCID 53666165, compound

HRID 652579Notes

Reaction equation

HRID 652579 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:26])([CH3:25])[C:5]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[N:23]O)[CH3:22])=[CH:17][CH:16]=1)([OH:12])[CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1.[Cl:27][C:28]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:29]=1[CH2:30]Cl.O>CS(C)=O.C(O)(=O)C>[Cl:27][C:28]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:29]=1[CH2:30][N:23]=[C:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C:5]([OH:12])([C:4]([CH3:26])([CH3:25])[CH3:3])[CH2:6][N:7]2[CH:11]=[N:10][CH:9]=[N:8]2)=[CH:16][CH:17]=1)[CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 86740378HCID 86740378, compound

Product 1

HCID 53666165HCID 53666165, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

1.44 g (0.06 mol) of sodium hydride (80% strength in paraffin oil) are added to a solution of 14.94 g (0.045 mol) of 3,3-dimethyl-2-[4-(1-hydroximinoethyl)phenoxymethyl]-1-(1,2,4-triazol-1-yl)-2-butanol (Example 2) in 120 ml of absolute dimethylsulphoxide. The reaction mixture is stirred at room temperature for about 1 hour, until a clear solution has formed. 8.33 ml (0.06 mol) of 2,4-dichlorobenzyl chloride are then added and the reaction mixture is subsequently stirred at room temperature for 1.5 hours. Thereafter, water and glacial acetic acid are carefully added and the mixture is concentrated. The residue is taken up in ethyl acetate and the mixture is washed several times with dilute sodium chloride solution, dried over sodium sulphate and concentrated. The residue is chromatographed over a silica gel column (methylene chloride/ethyl acetate=4:1) and the product is recrystallized from acetonitrile. 16.2 g (73% of theory) of 2-{4-[1-(2,4-dichlorobenzylimino)-ethyl]phenoxymethyl} -3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanol of melting point 101° C. are obtained.

Workup

  1. customhas formed
  2. stirringthe reaction mixture is subsequently stirred at room temperature for 1.5 hours
  3. concentrationthe mixture is concentrated
  4. washthe mixture is washed several times with dilute sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue is chromatographed over a silica gel column (methylene chloride/ethyl acetate=4:1)
  8. customthe product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b1f544a38fe44776be9e5389d65672c8
Source dataset
uspto-grants-1987_06
Patent number
US04672134

Reaction notes

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