Dimethylformamide → HCID 59140413, compound

HRID 425326Notes

Reaction equation

HRID 425326 reaction equation
C([Li])CCC.[CH3:6][C:7]([CH3:21])([CH3:20])[CH2:8][C:9]1[N:10]=[CH:11][N:12]([S:14]([N:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])[CH:13]=1.CN(C)[CH:24]=[O:25]>O1CCCC1>[CH3:6][C:7]([CH3:21])([CH3:20])[CH2:8][C:9]1[N:10]=[C:11]([CH:24]=[O:25])[N:12]([S:14]([N:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])[CH:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 591403964-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamideHCID 178418339Butyllithium

Product 1

HCID 59140413HCID 59140413, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (2.5 M in hexane) (0.83 mL, 2.2 mmol) was added to a −78° C. solution of 4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (54 mg, 2.2 mmol) in tetrahydrofuran (5 mL). After stirring at −78° C. for 10 min, N,N-dimethylformamide (0.17 mL, 2.2 mmol) was added and the reaction allowed to warm to ambient temperature. After stirring at ambient temperature for a further 5 min, the reaction mixture was quenched with water and extracted with methylene chloride. The combined aqueous phases were dried (magnesium sulfate) and concentrated. Chromatography over silica eluting with 0-80% ethyl acetate/hexane afforded the title compound.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringAfter stirring at ambient temperature for a further 5 min
  3. customthe reaction mixture was quenched with water
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined aqueous phases were dried (magnesium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d97bf19f804042349e784cd48951862c
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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