Dimethylformamide → HCID 70150069, compound

HRID 2292663Notes

Reaction equation

HRID 2292663 reaction equation
[N:1]1[NH:2][N:3]=[CH:4][CH:5]=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](CBr)=[CH:17][C:16]=1[Cl:23])=[O:13].[CH3:26]N(C)C=O>>[CH3:25][C:11]([CH3:10])([CH3:24])[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)=[C:17]([CH3:26])[C:16]=1[Cl:23])=[O:13]

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 675161H-1,2,3-TriazoleHCID 21833670HCID 21833670, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70150069HCID 70150069, compound

Conditions

Temperature
10 °C

Procedure

A mixture of 2H-1,2,3-triazole (2.26 g), sodium hydride (60%, 1.31 g) and anhydrous N,N-dimethylformamide (100 ml) 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 4-bromomethyl-2-chlorophenyl 2,2-dimethylpropanoate (10 g) 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-964015d45a8b46b1ab4ef83c728c1796
Source dataset
uspto-grants-1997_11
Patent number
US05684022

Reaction notes

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