Sodium hydride → HCID 21833674, compound

HRID 1418711Notes

Reaction equation

HRID 1418711 reaction equation
[H-].[Na+].[N:3]1([CH2:8][C:9]2[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15][OH:16])=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[N:4]1.Br[C:20]1[S:21][CH:22]=[CH:23][N:24]=1>CN(C)C=O.CS(C)=O>[S:21]1[CH:22]=[CH:23][N:24]=[C:20]1[O:16][CH2:15][CH2:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][N:3]2[CH:7]=[CH:6][CH:5]=[N:4]2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 764302-BromothiazoleHCID 21833673HCID 21833673, compound

Product 1

HCID 21833674HCID 21833674, compoundYield 40.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 10 ml of anhydrous N,N-dimethylformamide and 110 mg of sodium hydride (60% oil dispersion) was added dropwise an anhydrous dimethylsulfoxide (5 ml) solution of 500 mg of 2-[4-(1-pyrazolyl)methylphenoxy]ethanol (produced in Reference Production Example 1 described below) under stirring over 10 minutes. After stirring at 60° to 70° C. for 2 hours, the mixture was cooled to 5° to 10° C., to which an anhydrous N,N-dimethylformamide (5 ml) solution of 488 mg of 2-bromothiazole was added dropwise over 10 minutes. The mixture was then stirred at room temperature over-night and then at 60° to 70° C. for further 2 hours. The reaction mixture was poured into 50 ml of ice water, which was extracted with twice with 30 ml of toluene. The organic layers were combined, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 280 mg of 4-(1-pyrazolyl)methylphenyl 2-(2-thiazolyl-oxy)ethyl ether (compound 5). Yield, 41%.

Workup

  1. stirringAfter stirring at 60° to 70° C. for 2 hours
  2. additionwas added dropwise over 10 minutes
  3. stirringThe mixture was then stirred at room temperature over-night
  4. waitat 60° to 70° C. for further 2 hours
  5. extractionwas extracted with twice with 30 ml of toluene
  6. washwashed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-518a1e74f9194b27b6597244ba0d3b69
Source dataset
uspto-grants-1999_03
Patent number
US05883262

Reaction notes

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