Sulfuryl chloride → 2,2,2-trichloro-1-(4-chloro-1H-pyrrol-2-yl)ethan-1-one

HRID 1172797Notes

Reaction equation

HRID 1172797 reaction equation
[Cl:1][C:2]([Cl:11])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].S(Cl)([Cl:15])(=O)=O>C(Cl)Cl>[Cl:11][C:2]([Cl:1])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[C:8]([Cl:15])[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 3214872-(Trichloroacetyl)pyrrole

Product 1

HCID 71306882,2,2-trichloro-1-(4-chloro-1H-pyrrol-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethanone (1 eq.) in dry DCM (1 M) at 0° C. was added sulfuryl chloride (1.15 eq.) dropwise. The mixture was stirred overnight at RT, washed with water (2×) and sat. aq. NaHCO3 solution. The organic phase was separated, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by on chromatography on silica gel, eluting with petroleum ether/Et2O to afford the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ: 9.45 (1H, br. S), 7.26 (1H, s), 7.09 (1H, s).

Workup

  1. washwashed with water (2×) and sat. aq. NaHCO3 solution
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by on chromatography on silica gel
  6. washeluting with petroleum ether/Et2O

Sources & evidence

ORD record
ord-3e38265d867645799d5aef9d4f7cf810
Source dataset
uspto-grants-2010_11
Patent number
US07834015B2

Reaction notes

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