Water → HCID 11796154, compound

HRID 256596Notes

Reaction equation

HRID 256596 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[C:18](=[O:23])[C:19]([Cl:22])([Cl:21])[Cl:20])[CH2:11][C:10](=[O:12])[NH:9][C:7]1=[O:8])=[O:5])[CH3:2].S(Cl)([Cl:27])(=O)=O.O>C(Cl)(Cl)Cl>[Cl:27][C:16]1[CH:15]=[C:14]([C:18](=[O:23])[C:19]([Cl:22])([Cl:20])[Cl:21])[N:13]([C:6]2([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][C:10](=[O:12])[NH:9][C:7]2=[O:8])[CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 10667564HCID 10667564, compound

Product 1

HCID 11796154HCID 11796154, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 2-ethoxycarbonyl-2-(2-trichloroacetylpyrrol-1-yl)succinimide (6.0 g) in chloroform (50 ml) was added dropwise a solution of sulfuryl chloride (4.8 g) in chloroform (5 ml) under ice cooling. The resulting mixture was stirred under ice cooling for 30 minutes, poured into water, and extracted with chloroform. The extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel using n-hexane/ethyl acetate (2:1) as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (2.5 g, 41.7%) as colorless crystals, mp 182°-185° C.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extracts were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on silica gel
  5. additionFractions containing the title compound
  6. customevaporated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-75c3a3072c33450d9948e44858a1376b
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Reaction notes

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