Thionyl Chloride → 4-[3-chloromethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazol-4-ylmethyl]pyridine hydrochloride

HRID 1862469Notes

Reaction equation

HRID 1862469 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH:15]([CH3:17])[CH3:16])[N:13]=[C:12]([CH2:18]O)[C:11]=2[CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(Cl)([Cl:29])=O>ClCCl>[ClH:1].[Cl:29][CH2:18][C:12]1[C:11]([CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)[N:14]([CH:15]([CH3:17])[CH3:16])[N:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 514441[5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methanol

Product 1

HCID 693533844-[3-chloromethyl-5-(3,5-dichlorophenylthio)-1-isopropyl-1H-pyrazol-4-ylmethyl]pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution containing 108 mg of 5-(3,5-dichlorophenylthio)-1-isopropyl-4-[(4-pyridyl)methyl]-1H-pyrazole-3-methanol in 5 ml of anhydrous dichloromethane at −78° C. under nitrogen was treated with 45 μl of thionyl chloride. The mixture was stirred for 1 h and left to warm to room temperature. The solvent was removed under reduced pressure and the residue was azeotroped with toluene to give 120 mg of 4-[3-chloromethyl-5-(3,5-dichloro-phenylthio)-1-isopropyl-1H-pyrazol-4-ylmethyl]pyridine hydrochloride as a white solid which was used without further purification. Mass spectrum (ESI) 426 [M+H]+.

Workup

  1. waitleft
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-2e15553b98c6432e9a1b657f87ddb8a1
Source dataset
uspto-grants-2003_03
Patent number
US06538015B1

Reaction notes

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