Thionyl Chloride → HCID 23249595, compound

HRID 1890262Notes

Reaction equation

HRID 1890262 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([C:11]2[CH:15]=[C:14]([CH2:16]O)[NH:13][N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CN(C)C=O.ClCCl>[Cl:3][CH2:16][C:14]1[NH:13][N:12]=[C:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:15]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 113896805-Phenyl-1H-pyrazole-3-methanol

Product 1

HCID 23249595HCID 23249595, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

At 20° C., 6.1 ml of thionyl chloride and 10 drops of dimethylformamide are added to a solution of 7.3 g (42.0 mmol) of (3-phenyl-1H-pyrazol-5-yl)methanol in 220 ml of dichloromethane. The mixture is then boiled under reflux for 12 h. The solvent is then removed from the reaction mixture. The residue is taken up in 100 ml of dichloromethane, and a saturated sodium bicarbonate solution is added to the mixture until a pH of from 6 to 7 is established. The mixture is then freed from the solvent under reduced pressure and dried. This gives 5.65 g of the desired product which is reacted further without further purification; log P(HCOOH): 2.05 with MS (ESI): 193.1/195.1 ([M+H]+).

Workup

  1. temperatureunder reflux for 12 h
  2. customThe solvent is then removed from the reaction mixture
  3. additiona saturated sodium bicarbonate solution is added to the mixture until a pH of from 6 to 7
  4. customdried
  5. customThis gives 5.65 g of the desired product which is reacted further without further purification

Sources & evidence

ORD record
ord-13ca3a9c27964ca485182f7c3b2f6dcc
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

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