Water → HCID 25044530, compound

HRID 1807429Notes

Reaction equation

HRID 1807429 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Cl:11][C:12]1[CH:13]=[C:14]([S:19](Cl)(=[O:21])=[O:20])[CH:15]=[C:16]([Cl:18])[CH:17]=1.O.C(OCC)(=O)C>N1C=CC=CC=1>[Cl:18][C:16]1[CH:15]=[C:14]([S:19]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)(=[O:20])=[O:21])[CH:13]=[C:12]([Cl:11])[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 788675-AminoindoleHCID 5223883,5-Dichlorobenzenesulfonyl chloride

Product 1

HCID 25044530HCID 25044530, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.5 g 5-aminoindole are dissolved in 25 ml of pyridine. To this are added 4.64 g of 3,5-dichlorophenylsulphonyl chloride and the mixture is stirred for 4 hours at ambient temperature. The solvent is eliminated in vacuo and the residue is divided between water and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 10:1 to 1:5).

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. washthe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialAfter drying with magnesium sulphate the solvents
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 10:1 to 1:5)

Sources & evidence

ORD record
ord-836bb999d201434497be63a1dc2bef88
Source dataset
uspto-grants-2013_01
Patent number
US08357689B2

Reaction notes

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