Dimethylformamide → HCID 23024748, compound

HRID 350097Notes

Reaction equation

HRID 350097 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:19]1([C:25]2[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][NH:27][N:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C)C=O>O>[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:27]2[CH:28]=[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:26]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 700424-Benzyloxybenzyl chlorideHCID 178469912HCID 178469912, compound

Product 1

HCID 23024748HCID 23024748, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60%, oily, 1.85 g) was added to a mixture of 4-benzyloxybenzyl chloride (10.8 g), ethyl 3-phenyl-1H-pyrazole-4-carboxylate (10.0 g) and N,N-dimethylformamide (50 ml) at 0° C., and the mixture was stirred for 1.5 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The colorless crystals obtained were collected by filtration to yield ethyl 1-(4-benzyloxybenzyl)-3-phenyl-1H-pyrazole-4-carboxylate (15.3 g, yield: 80%). This was crystallized from ethyl acetate-diisopropyl ether. Melting point: 102–103° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe colorless crystals obtained
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-0a2b5a2dcd9a493399ef20655b944712
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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