1-Chloro-4-(chloromethyl)benzene → 1-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propan-1-one

HRID 851622Notes

Reaction equation

HRID 851622 reaction equation
[CH3:1][C:2]1([C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH2:7][O:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C)C=O>[CH3:1][C:2]1([C:8](=[O:15])[CH:9]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH2:23][C:22]2[CH:25]=[CH:26][C:19]([Cl:18])=[CH:20][CH:21]=2)[CH2:7][O:6][CH2:5][O:4][CH2:3]1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 128556521-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one

Product 1

HCID 128556531-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propan-1-oneYield 66.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of 105.5 g (0.5 mole) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one in 100 ml of dimethylformamide is added dropwise, at 20°-25° C., to a suspension, stirred under pure nitrogen, of 13.2 g (0.55 mole) of sodium hydride in 100 ml of dry dimethylformamide. The reaction mixture is then stirred for three hours at 25° C., after which a solution of 81 g (0.5 mole) of 4-chlorobenzyl chloride in 50 ml of dimethylformamide is added dropwise and stirring is then continued for 14 hours. 50 ml of ice water are then cautiously added dropwise and the mixture is concentrated under reduced pressure. The residue is partitioned between 400 ml of methylene chloride and 200 ml of water and the organic phase is washed with three times 200 ml of water, dried over Na2SO4 and evaporated down. 112 g (66.8%) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propan-1-one are obtained as a pale yellow resin.

Workup

  1. stirringstirring
  2. waitis then continued for 14 hours
  3. concentrationthe mixture is concentrated under reduced pressure
  4. customThe residue is partitioned between 400 ml of methylene chloride and 200 ml of water
  5. washthe organic phase is washed with three times 200 ml of water
  6. dry with materialdried over Na2SO4
  7. customevaporated down

Sources & evidence

ORD record
ord-bc7236ccd955423fbb48b5be287711d8
Source dataset
uspto-grants-1983_05
Patent number
US04385925

Reaction notes

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