Sulfuryl chloride → HCID 18630151, compound

HRID 534831Notes

Reaction equation

HRID 534831 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:18])(=O)=O>C(O)(=O)C>[C:1]([C:5]1[CH:10]=[C:9]([Cl:18])[CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:14])[CH3:13])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 343805N-(2-tert-butylphenyl)acetamide

Product 1

HCID 18630151HCID 18630151, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-(2-tert-butylphenyl)acetamide (Reference Example 17, 5.93 g, 31.0 mmol) and sulfuryl chloride (10.5 g, 77.5 mmol) in acetic acid (190 mL) was stirred at 50° C. for 16 h. The reaction mixture was partitioned between ethyl acetate and water, and the organic layer was washed with 10% aqueous NaHCO3, and saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting solid was recrystallized from toluene/diethyl ether to give the title compound (3.73 g) as a white solid. The mother liquid was concentrated under reduced pressure and the residue was purified by flash column chromatography (silica gel, 4:1-1:4 hexane/ethyl acetate) to provide the title compound (1.05 g) as a white solid.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with 10% aqueous NaHCO3, and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solid was recrystallized from toluene/diethyl ether

Sources & evidence

ORD record
ord-7775d21209f441daba1dfce70ef1324b
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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