Thionyl Chloride → 2-Chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methylimidazole

HRID 1416017Notes

Reaction equation

HRID 1416017 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16]O)=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(Cl)([Cl:23])=O>CN(C)C=O>[Cl:23][CH2:16][C:13]1[N:14]([CH3:15])[C:10]([S:9][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)=[C:11]([CH:18]([CH3:20])[CH3:19])[N:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 473916(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanol

Product 1

HCID 221306052-Chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methylimidazoleYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To dry dimethylformamide (50 ml)solution of 22.5 g (67.9 mmol)of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methanol (Compound I-8)was added 25.0 ml of thionyl chloride, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and to the residue, ethyl acetate was added and extracted. The extract was neutralized with a saturated aqueous sodium hydrogen carbonate solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give 23.7 g of 2-chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methylimidazole (28a)(yield about 100%). mp 110-111° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue, ethyl acetate was added
  3. extractionextracted
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4a3d629626b2428685486b78f02dc114
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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