Sulfuryl chloride → HCID 21266811, compound

HRID 566603Notes

Reaction equation

HRID 566603 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([CH3:21])[N:16]([CH:18]([F:20])[F:19])[CH:17]=2)=[CH:9][CH:8]=1.C(=O)([O-])O.[Na+]>ClC(Cl)(Cl)Cl>[Cl:4][C:17]1[N:16]([CH:18]([F:20])[F:19])[C:15]([CH3:21])=[N:14][C:13]=1[C:10]1[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 21266775HCID 21266775, compound

Product 1

HCID 21266811HCID 21266811, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

26.7 g (0.19 mol) of sulfuryl chloride were added dropwise with ice-cooling to a suspension of 24 g (98 mmol) of 4-(4-chlorophenyl)-1-difluoromethyl-2-methyl-1H-imidazole in 200 ml of tetrachloromethane. After the reaction mixture had been stirred for 2 hours, an excess of saturated aqueous sodium hydrogen carbonate solution was added dropwise (still with ice-cooling). The solids were subsequently filtered off. The organic phase was washed with water until neutral, dried over magnesium sulfate and concentrated. The crude product was purified by means of silica gel column chromatography (eluent: hexane/ethyl acetate=8:1). Yield: 7.4 g.

Workup

  1. temperaturecooling)
  2. filtrationThe solids were subsequently filtered off
  3. washThe organic phase was washed with water until neutral,
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by means of silica gel column chromatography (eluent: hexane/ethyl acetate=8:1)

Sources & evidence

ORD record
ord-542adfdd6b314c35abd95e574f75bc6e
Source dataset
uspto-grants-2001_01
Patent number
US06175007B1

Reaction notes

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