Thionyl Chloride → 4-(chloromethyl)-5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazole

HRID 2261322Notes

Reaction equation

HRID 2261322 reaction equation
[N:1]1([C:6]2[N:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:9]=[CH:8][C:7]=2[CH2:15]O)[CH:5]=[CH:4][CH:3]=[CH:2]1.S(Cl)([Cl:19])=O>ClCCl>[Cl:19][CH2:15][C:7]1[CH:8]=[N:9][N:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[N:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57736270[5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazol-4-yl]methanol

Product 1

HCID 577363114-(chloromethyl)-5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.20 g of [5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazol-4-yl]methanol was dissolved in 20 ml of dichloromethane, and 0.73 ml of thionyl chloride was added. The mixture was stirred at room temperature for 1.5 hours and then concentrated under reduced pressure. After aqueous saturated sodium hydrogen carbonate was added, the residue was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.35 g of 4-(chloromethyl)-5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazole.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionAfter aqueous saturated sodium hydrogen carbonate was added
  3. extractionthe residue was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7efbb563fab4e128433db3de83277f3
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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