Dimethylformamide → HCID 22130341, compound

HRID 1857735Notes

Reaction equation

HRID 1857735 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:5][C:6]1[N:10]([CH3:11])[C:9]([CH2:12]O)=[N:8][C:7]=1[CH:14]([CH3:16])[CH3:15].CN(C)C=O.[N-:26]=[N+:27]=[N-:28].[Na+]>S(Cl)(Cl)=O.O>[N:26]([CH2:12][C:9]1[N:10]([CH3:11])[C:6]([CH2:5][C:4]2[CH:3]=[C:2]([Cl:1])[CH:19]=[C:18]([Cl:20])[CH:17]=2)=[C:7]([CH:14]([CH3:16])[CH3:15])[N:8]=1)=[N+:27]=[N-:28]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 22130877HCID 22130877, compound

Product 1

HCID 22130341HCID 22130341, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

In 5 ml of thionyl chloride was dissolved 160 mg (0.51 mmol) of [5-(3,5-dichlorobenzyl)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methanol (59a), and the mixture was stirred at room temperature. After 2 hours, the reaction mixture was concentrated under reduced pressure, and to the residue, 5 ml of dry dimethylformamide and 80 mg (1.23 mmol) of sodium azide were added. The mixture was stirred at room temperature for 3 hours, diluted with water, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated to give 150 mg of 2-azidomethyl-5-(3,5-dichlorobenzyl)-4-isopropyl-1-methyl-1H-imidazole (60) (yield 87%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. stirringThe mixture was stirred at room temperature for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-839df402e1b741f6b6bd2be0999623f6
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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