Sodium Sulfate → Ethyl 3-phenylsulfonyl-5-chloroindole-2-carboxylate

HRID 260478Notes

Reaction equation

HRID 260478 reaction equation
C1(S[C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=3)[NH:10][C:9]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])C=CC=CC=1.[O-:23][S:24]([O-:27])(=O)=O.[Na+].[Na+].Cl[C:31]1[CH:32]=[C:33]([CH:38]=[CH:39][CH:40]=1)C(OO)=O>C(Cl)(Cl)Cl>[C:31]1([S:24]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=3)[NH:10][C:9]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:27])=[O:23])[CH:32]=[CH:33][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 70297m-Chloroperbenzoic acidHCID 15035363ethyl 5-chloro-3-(phenylthio)-1H-indole-2-carboxylate

Product 1

HCID 22401503Ethyl 3-phenylsulfonyl-5-chloroindole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

Ethyl 3-phenylthio-5-chloroindole-2-carboxylate (642 mg, 1.94 mmol) was dissolved in chloroform (35 mL) and a dried (Na2SO4) solution of m-chloroperoxybenzoic acid (55% pure, 1.30 g, 4.1 mmol) in chloroform (20 mL) was added dropwise. The progress of the oxidation was monitored by tlc until complete. After 5 hours, the reaction was diluted with chloroform and some methanol and the solution washed with aq. NaHCO3 and aq. Na2CO3. The dried (Na2SO4) organic layer was filtered through a pad of charcoal and the solvents removed under reduced pressure. The residue was triturated with diethyl ether to yield the product. Crystallization from methylene chloride and diethyl ether gave analytically pure material, mp 201°-202° C.

Workup

  1. additionwas added dropwise
  2. washsome methanol and the solution washed with aq. NaHCO3 and aq. Na2CO3
  3. dry with materialThe dried (Na2SO4) organic layer
  4. filtrationwas filtered through a pad of charcoal
  5. customthe solvents removed under reduced pressure
  6. customThe residue was triturated with diethyl ether
  7. customto yield the product
  8. customCrystallization from methylene chloride and diethyl ether
  9. customgave analytically pure material, mp 201°-202° C.

Sources & evidence

ORD record
ord-7dfdef450b614492b008d81f7e5aa352
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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