2-Thiophenesulfonyl chloride → HCID 57901695, compound

HRID 1851482Notes

Reaction equation

HRID 1851482 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:16][CH2:17][CH2:18][CH3:19])=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[CH2:17]([S:16][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:25]([C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)(=[O:27])=[O:26])=[C:10]2[C:6]=1[CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:9]2)[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 67109617HCID 67109617, compound

Product 1

HCID 57901695HCID 57901695, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixed solution of ethyl 7-amino-4-(propylthio)-1H-indole-2-carboxylate (0.90 g) and pyridine (10 mL) was added 2-thiophenesulfonyl chloride (0.72 g) under ice-cooling, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:9-1:3), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (0.64 g, yield 47%) as colorless needle crystals. melting point 150-151° C.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-252ccb5a1d4d4b79a5444afb600beeb5
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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