Water → HCID 53850736, compound

HRID 2270561Notes

Reaction equation

HRID 2270561 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].[C:8]([O:12][C:13]([N:15]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1F)=[O:14])([CH3:11])([CH3:10])[CH3:9].O>CS(C)=O>[C:8]([O:12][C:13]([N:15]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 24758Sodium hydrideHCID 22981229HCID 22981229, compound

Product 1

HCID 53850736HCID 53850736, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a mixture of pyrazole (1.0 g) and dimethylsulfoxide (50 ml), sodium hydride (0.54 g) was added under ice cooling. The reaction mixture was stirred under ice cooling for 1 h and then a solution of N-(2-fluoro-5-nitrophenylmethyl)iminodicarboxylic acid di-t-butyl ester (5.0 g) in dimethyl sulfoxide (50 ml) was added. The reaction mixture was stirred at room temperature for 15 h and, after addition of water, subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=1:4) to give the titled compound (yield, 73%).

Workup

  1. additionwas added under ice cooling
  2. stirringThe reaction mixture was stirred at room temperature for 15 h
  3. extractionsubjected to extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-a0cd17a22c5348a8af533b4859720e32
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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