Sodium hydride → HCID 66769059, compound

HRID 606462Notes

Reaction equation

HRID 606462 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9].[N+]([C:16]1[N:20]=[CH:19][N:18]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:17]=1)([O-])=O.[H-].[Na+]>C1COCC1>[C:34]1([C:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:18]2[CH:19]=[N:20][C:16]([O:1][CH2:2][CH2:3][O:4][C:5]3[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=3)[C:8]#[N:9])=[N:17]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 122221843-(2-hydroxyethoxy)benzonitrileHCID 667692413-nitro-1-(triphenylmethyl)-1H-1,2,4-triazole

Product 1

HCID 66769059HCID 66769059, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-[(2-hydroxyethyl)oxy]benzonitrile obtained in Reference Example 30 (19.2 g, 118 mmol) in THF (100 mL) was added dropwise to a suspension of 3-nitro-1-(triphenylmethyl)-1H-1,2,4-triazole obtained in Reference Example 33 (40.0 g, 112 mmol) and 60% sodium hydride (oil dispersion, 6.06 g, 151.52 mmol) in THF (300 mL), and the mixture was stirred at room temperature for 12 hr. The mixture was cooled to 0° C., and extracted with water and ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (0-30% ethyl acetate/hexane) to give the title compound as a white powder (25.0 g, 46%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionextracted with water and ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (0-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-caa52651b0394dd59fde8fe62b0f8e9b
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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