Water → HCID 13488631, compound

HRID 978310Notes

Reaction equation

HRID 978310 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:23])([C:17]([CH:20]2[CH2:22][CH2:21]2)([CH3:19])[CH3:18])[CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[CH:6][CH:5]=1.[CH3:24]I.O>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([O:23][CH3:24])([C:17]([CH:20]2[CH2:21][CH2:22]2)([CH3:19])[CH3:18])[CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13488624HCID 13488624, compound

Product 1

HCID 13488631HCID 13488631, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.8 g NaH 80% in 25 ml DMF are added dropwise, at room temperature, a solution of 7.64 g 2-(4-chlorophenyl)-3-cyclopropyl-3-methyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol in 50 ml DMF. The reaction is stirred at 40° for 30 minutes. Then are added dropwise, at 50°, 3.76 g CH3I. The mixture is stirred for 18 hours at 20°, then poured into one liter of water and extracted with CH2Cl2. The organic phases are washed with water, dried over MgSO4 and concentrated by continuous flask evaporation. The title compound is then obtained by chromatography of the residue on silica gel (mobile phase diethylether/triethylamine 10:2) in the form of white crystals, m.p. 87°-89°.

Workup

  1. additionare added dropwise, at room temperature
  2. additionThen are added dropwise, at 50°
  3. stirringThe mixture is stirred for 18 hours at 20°
  4. extractionextracted with CH2Cl2
  5. washThe organic phases are washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated by continuous flask
  8. customevaporation

Sources & evidence

ORD record
ord-d4ebc9c411554a6b84a1961f240a4a82
Source dataset
uspto-grants-1987_05
Patent number
US04664696

Reaction notes

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