Sodium hydride → HCID 53869820, compound

HRID 1740824Notes

Reaction equation

HRID 1740824 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].[H][H].[CH3:10][C:11]([CH3:25])([CH3:24])[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][C:16]=1[Cl:23])=[O:13]>CN(C)C=O>[CH3:10][C:11]([CH3:25])([CH3:24])[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)=[CH:17][C:16]=1[Cl:23])=[O:13]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 21833670HCID 21833670, compoundHCID 178418361HCID 178418361, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 53869820HCID 53869820, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
10 °C

Procedure

A mixture of 2.26 g of 2H- 1,2,3-triazole, 1.31 g of sodium hydride (60% oil dispersion) and 100 ml of anhydrous N,N-dimethylformamide was stirred at 60° to 70° C. under a nitrogen atmosphere for 2 hours. After the evolution of hydrogen gas ceased, the mixture was cooled to 10° C. To this mixture was added dropwise an anhydrous N,N-dimethylformamide (150 ml) solution of 10 g of 4-bromomethyl-2-chlorophenyl 2,2-dimethylpropanoate at room temperature under stirring over 1 hour, and the mixture was stirred at 80° C. for 1 hour. After cooling, the reaction mixture was poured into ice water, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 2-chloro-4-(2-2H-1,2,3-triazolyl)methylphenyl 2,2-dimethylpropanoate.

Workup

  1. stirringunder stirring over 1 hour
  2. stirringthe mixture was stirred at 80° C. for 1 hour
  3. temperatureAfter cooling
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous ammonium chloride solution
  6. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d7e7f6dccec4fdfa8ddc7f9c5ba96b3
Source dataset
uspto-grants-1999_10
Patent number
US05972949

Reaction notes

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